Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:10][O:11][C:12](=[O:33])[CH:13]=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1
Reactant: Cc1ccc(C=O)cc1
Reactant: COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
Solvent: ClCCl
Product: COC(=O)C=Cc1ccc(C)cc1
Temperature: 90 °C
Reaction time: 8 h
Yield: 94.8 %

Procedure:
1 g of p-tolualdehyde (8.3 mM) and 4.16 g of triphenyl phosphanyliden-acetic acid methyl ester (12.45 mM) were dissolved in methylene chloride, the reaction solution was stirred at 90° C. for overnight. After the resluting mixture was concentrated under reduced pressure, a solvent mixture mixed with EtOAc and hexane (1:7) was added thereto with stirring for 1 hr. And then white solid was removed on filter, the residue was filtered and concentrated in vacuo to give 1.39 g of 3-p-tolyl-acrylic acid methyl ester (40aa) (yield: 95%).
Reaction SMILES: [NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH3:9].S=[C:13]1[CH2:17][S:16][C:15](=[O:18])[NH:14]1>C(O)C>[CH2:10]([N:7]([CH2:8][CH3:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:13]1[CH2:17][S:16][C:15](=[O:18])[N:14]=1)[CH3:11]
Reactant: CCN(CC)CCOCCN
Reactant: O=C1NC(=S)CS1
Solvent: CCO
Product: CCN(CC)CCOCCNC1=NC(=O)SC1
Temperature: 25 °C
Reaction time: 8 h
Yield: 54 %

Procedure:
To a solution of 2-(2-aminoethoxy)-N,N-diethylethanamine (2.23 g) in ethanol (50 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.76 g), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (1.85 g).
Reaction SMILES: [OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[O:13]([CH2:20][CH2:21]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.C(OCC)C>[O:13]([CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
Reactant: BrCCOc1ccccc1
Reactant: O=C1CCCc2cc(O)ccc21
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: CCOCC
Solvent: CN(C)C=O
Solvent: O
Product: O=C1CCCc2cc(OCCOc3ccccc3)ccc21
Temperature: 100 °C
Yield: 73.5 %

Procedure:
A mixture of 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (2.5 g), 2-phenoxyethyl bromide (3.4 g) and cesium carbonate (5.5 g) were stirred in N,N-dimethylformamide (15 cm3) and heated at 100° C. for 2.5 h. The reaction mixture was allowed to cool to room temperature and then diluted with water (150 cm3). The aqueous mixture was extracted with ethyl acetate (2×50 cm3) and the organic extracts were washed with aqueous sodium hydroxide (1 M, 50 cm3), water (50 cm3) and then hydrochloric acid (2 M, 50 cm3). The organic extracts were dried (Na2SO4) and the solvent removed under reduced pressure to afford the crude product which was suspended in diethyl ether and filtered to yield the title compound (3.2 g).
Reaction SMILES: [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14](Cl)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([F:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:13]=2[C:14]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([F:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1
Reactant: COc1cc(NS(=O)(=O)c2ccc(Cl)cc2)c(C(=O)Cl)cc1OC
Reactant: Nc1ccc(S(=O)(=O)F)cc1
Solvent: Cc1ccccc1
Product: COc1cc(NS(=O)(=O)c2ccc(Cl)cc2)c(C(=O)Nc2ccc(S(=O)(=O)F)cc2)cc1OC

Procedure:
10.00 g (25.6 mmol) of 2-(4-Chloro-phenylsulfonylamino)-4,5-dimethoxy-benzoyl chloride were mixed with 300 ml of toluene, 4.49 g (25.6 mmol) of 4-aminobenzenesulfonyl fluoride were added and the mixture was heated under reflux for 4 h. After cooling the precipitated solid was filtered off with suction and washed with toluene. 11.71 g (87%) of the title compound having a melting point of 216-219° C. were obtained.
Reaction SMILES: [N+:1]([C:4]1[C:21]2[C:22]3[C:7]([C:8]4[C:23]5[C:12]6=[C:13]([C:24]([N:26]([CH:29]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:27](=[O:28])[C:11]6=[CH:10][CH:9]=4)=[O:25])[CH:14]=[CH:15][C:16]=5[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[CH:6][CH:5]=1)([O-])=O.O.[OH-].[K+].[C:45](O)(=[O:47])[CH3:46]>[Fe]>[C:45]([NH:1][C:4]1[C:21]2[C:22]3[C:7]([C:8]4[C:23]5[C:12]6=[C:13]([C:24]([N:26]([CH:29]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:27](=[O:28])[C:11]6=[CH:10][CH:9]=4)=[O:25])[CH:14]=[CH:15][C:16]=5[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[CH:6][CH:5]=1)(=[O:47])[CH3:46]
Reactant: CCCCCCC(CCCCCC)N1C(=O)c2ccc3c4cccc5c([N+](=O)[O-])ccc(c6ccc(c2c36)C1=O)c54
Reactant: CC(=O)O
Agent: [Fe]
Agent: [K+]
Agent: [OH-]
Solvent: O
Product: CCCCCCC(CCCCCC)N1C(=O)c2ccc3c4cccc5c(NC(C)=O)ccc(c6ccc(c2c36)C1=O)c54

Procedure:
100 mg (0.18 mmol) of 9-nitro-N-(1-hexylheptyl)perylene-3,4-dicarboximide (10) are suspended in 15 ml of glacial acetic acid, 80 mg (0.72 mmol) of iron dust are then added, and the red suspension is refluxed for 4.5 h, during which a slow colour change from red to red-brown and purple and then to dark-purple can be observed. First water is added to the cooled, violet solution, and the reaction mixture is then neutralized with 10 per cent KOH. The suspension which is now reddish purple is extracted three times with chloroform, the combined organic phases are dried with anhydrous sodium sulfate then evaporated on a rotary evaporator. According to the thin-layer chromatogram (chloroform/silica gel), the purple-coloured product obtained consists of 2 main products having Rf values of 0.02 and 0.43. This product is filtered by chromatography on silica gel using chloroform until the solution leaving the silica gel is no longer violet. The red-coloured silica gel is extracted with chloroform to give, after evaporation on a rotary evaporator, 50 mg of a red powder which is then recrystallized by extraction with methanol. Yield: 30 mg (30%) of 9-acetamido-N-(1-hexylheptyl)perylene-3,4-dicarboximide, m.p. >230° C.; from 172°-175° C. onwards product turns brown. Rf (CHCl3 /glacial acetic acid 20:1; silica gel)=0.90. UV (CHCl3): λmax (ε)=506 nm (31589, broad), 356 (2995). Fluorescence (CHCl3): λmax =574 nm (broad).
Reaction SMILES: [CH3:1][N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Br:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>ClCCl>[Br-:8].[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N+:2]1([CH3:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)[CH3:14]
Reactant: CCOC(=O)CBr
Reactant: CN1CCOCC1
Solvent: ClCCl
Product: CCOC(=O)C[N+]1(C)CCOCC1
Product: [Br-]
Temperature: 0 °C
Yield: 100.8 %

Procedure:
3.0 g (29.6 mmol) of 4-methylmorpholine was dissolved in 50 mL dichloromethane and cooled to 0° C. in an ice bath. To this solution 5.0 g of ethyl bromoacetate (29.6 mmol) was added dropwise with continuous stirring and the mixture was then allowed to warm to room temperature. The clear solution started to form white precipitate after 5 minutes of stirring at room temperature. The resulting mixture was stirred for another 3 h. The precipitate was isolated by vacuum filtration using a 30 mL glass fritted funnel and washed 3 times with 30 mL of acetone to give 8.0 g of the product as a white solid. Positive mode ESI/MS: m/z=188 (M+, minus Br); confirmed by 1H NMR.
Reaction SMILES: [CH3:1][N:2]1[CH2:7][CH2:6][P:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)(=[O:8])[CH2:4][CH2:3]1.[F:16][C:17]([F:23])([F:22])[S:18](N)(=[O:20])=[O:19]>CN(C=O)C>[F:16][C:17]([F:23])([F:22])[S:18]([O:15][C:12]1[CH:13]=[CH:14][C:9]([P:5]2(=[O:8])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:10][CH:11]=1)(=[O:20])=[O:19]
Reactant: NS(=O)(=O)C(F)(F)F
Reactant: CN1CCP(=O)(c2ccc(O)cc2)CC1
Solvent: CN(C)C=O
Product: CN1CCP(=O)(c2ccc(OS(=O)(=O)C(F)(F)F)cc2)CC1
Temperature: 25 °C
Reaction time: 16 h

Procedure:
4-(1-Methyl-4-oxido-1,4-azaphosphinan-4-yl)phenol (0.50 g, 2.22 mmol) was made 0.5 M in DMF and N-Phenyl-bis(trifluorometanesulfonamide (1.19 g, 3.33 mmol) was added, followed by TEA (0.62 mL, 4.44 mmol). The mixture was stirred at ambient temperature for 16 h then the precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was purified by HPLC (20-95% MeCN in water w/0.025% TFA). Pure fractions were identified, combined and concentrated in vacuo. The residue was taken up in EtOAc and washed with saturated aqueous sodium bicarbonate (1×) then dried (MgSO4) and concentrated in vacuo to afford the requisite product as a freebase. MS: cal'd 358 (MH+), exp 358 (MH
Reaction SMILES: [C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].O>CN(C=O)C>[C:4]([CH2:3][CH2:2][CH2:1][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])#[N:5]
Reactant: O=C1NC(=O)c2ccccc21
Agent: [K]
Solvent: CN(C)C=O
Solvent: O
Product: N#CCCCN1C(=O)c2ccccc2C1=O
Temperature: 90 °C
Reaction time: 2 h
Yield: 157.3 %

Procedure:
A mixture of potassium phthalimide (8.48 g, 0.046 mol) and 4-bromopropylcyanide (6.4 g, 0.043 mol) in 50 ml of anhydrous DMF was stirred at 90° C. for 2 h. After dilution with 300 ml of water, the aqueous solution was extracted with chloroform (80 ml×3). The combined chloroform solution was washed with 0.5% NaOH aqueous solution (80 ml) and water (100 ml), and dried over anhydrous Na2SO4. After evaporation of chloroform, an oil was obtained and 300 ml of water was added. The oil was rapidly solidified. The solid formed was collected by filtration, washed with water, and dried under high vacuum. The product was recrystallized from methanol which was diluted with water, to give white crystals (7.75 g, 84%). 1H NMR (CDCl3) δ 7.87 (dd, 2H), 7.75 (dd, 2H), 3.83 (t, 2H), 2.44 (t, 2H), 2.09 (quintet, 2H).
Reaction SMILES: C[S:2]([OH:5])(=[O:4])=[O:3].N[N:7]=[CH:8][NH:9][C:10]([C:12]1[N:13]([CH3:23])[C:14]2[C:19]([CH:20]=1)=[C:18]([CH3:21])[CH:17]=[CH:16][C:15]=2[OH:22])=[O:11].[N:24]1C=CC=CC=1>>[S:2]([OH:5])([O:22][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[C:19]2[C:14]=1[N:13]([CH3:23])[C:12]([C:10]([NH:9][C:8]([NH2:24])=[NH:7])=[O:11])=[CH:20]2)(=[O:4])=[O:3]
Reactant: c1ccncc1
Reactant: CS(=O)(=O)O
Reactant: Cc1ccc(O)c2c1cc(C(=O)NC=NN)n2C
Product: Cc1ccc(OS(=O)(=O)O)c2c1cc(C(=O)NC(=N)N)n2C
Temperature: 25 °C
Reaction time: 16.5 h

Procedure:
A sulfur trioxide-pyridine complex (2.51 g, 15.8 mmol) was added to a solution of N-(aminoiminomethyl)-1,4-dimethyl-7-hydroxy-1H-indole-2-carboxamide methanesulfonate (1.80 g, 5.26 mmol) in pyridine (20 ml), and the resulting mixture was stirred at room temperature for 16.5 hours. The solvent was distilled off under reduced pressure and water was added to the residue. Subsequently, diethyl ether was added thereto, and the solid precipitated was collected by filtration and washed with methanol to obtain 1.43 g of 2-[[[amino(imino)methyl]amino]carbonyl]-1,4-dimethyl-1H-indol-7-yl hydrogen sulfate.
Reaction SMILES: CI.N12CCCN=C1CCCC[CH2:4]2.[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([OH:24])=[O:23]>CC(C)=O>[CH3:14][C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:22]([O:24][CH3:4])=[O:23]
Reactant: C1CCC2=NCCCN2CC1
Reactant: CC1(c2ccccc2)CCC(=O)C=C1C(=O)O
Solvent: CI
Solvent: CC(C)=O
Product: COC(=O)C1=CC(=O)CCC1(C)c1ccccc1
Yield: 94.2 %

Procedure:
0.88 cm3 (14 mmol) of methyl iodide and 1.8 cm3 (12 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, dropwise, were successively added to a solution of 2.3 g (10 mmol) of (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylic acid in 20 cm3 of acetone. The reaction mixture was subsequently heated at reflux for two hours. The acetone was subsequently concentrated, the residue was then stirred with 100 cm3 of water and then extracted with three times 30 cm3 of ethyl acetate. After drying over magnesium sulphate and concentrating under reduced pressure, 2.3 g (94%) of methyl (RS)-2-methyl-5-oxo-2-phenylcyclohexene-1-carboxylate were obtained in the form of an orange oil, the characteristic of which was as follows:
Reaction SMILES: [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([O:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC([O:22][C:23](Cl)(Cl)Cl)=O.C([N:29](CC)CC)C.N>O1CCCC1>[C:23]([O:17][CH2:16][CH:15]([OH:18])[CH2:14][O:13][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)(=[O:22])[NH2:29]
Reactant: CCN(CC)CC
Reactant: O=C(Cl)OC(Cl)(Cl)Cl
Reactant: OCC(O)COc1cc(-c2cccc(Cl)c2)on1
Agent: N
Solvent: C1CCOC1
Product: NC(=O)OCC(O)COc1cc(-c2cccc(Cl)c2)on1
Reaction time: 0.5 h
Yield: 132.7 %

Procedure:
A solution of 10.0 g (37.0 mmoles) of 5-(m-chlorophenyl)-3-(2,3-dihydroxypropoxy)isoxazole [prepared as described in step (a) above] in 300 ml of dry tetrahydrofuran was cooled to 5° C., and then 3.96 g (20.0 mmoles) of trichloromethyl chloroformate were added dropwise to the mixture. The mixture was then stirred at 5°-6° C. for 30 minutes. At the end of this time, 4.04 g (40.0 mmoles) of triethylamine were added dropwise to the mixture at 5°-10° C., and the mixture was stirred at 3°-5° C. for 1 hour. 50 ml (400.0 mmoles) of 28% v/v aqueous ammonia were then added at one time, and the mixture was stirred at room temperature for a further 18 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was diluted with 400 ml of ethyl acetate. The mixture was then washed with 400 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation under reduced pressure to give a solid residue. This solid residue was recrystallized from ethyl acetate, to give 8.30 g (yield 72.1%) of the title compound as colorless scales, melting at 149°-150° C.
Reaction SMILES: [BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[C:13]([O:15][CH3:16])=[O:14])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:17]([O:19][CH3:20])=[O:18])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1
Reactant: COC(=O)C(=Cc1ccc(OC)cc1[N+](=O)[O-])C(=O)OC
Agent: Cl
Agent: [BH4-]
Agent: [Na+]
Solvent: CO
Product: COC(=O)C(Cc1ccc(OC)cc1[N+](=O)[O-])C(=O)OC
Temperature: 25 °C
Reaction time: 1 h
Yield: 75.5 %

Procedure:
Sodium borohydride (3.36 g) was added to a methanol (200 ml) solution of dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate (25 g) under ice-cooling. The reaction mixture was stirred at room temperature for one hour and then neutralized by adding dropwise 1N aqueous hydrochloric acid solution. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous potassium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to obtain the entitled compound (19 g).
Reaction SMILES: [NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10]C)=O.Cl[C:13]1[N:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>CO>[CH3:7][C:5]1[S:4][C:3]2[C:8](=[O:10])[N:18]3[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:13]3=[N:1][C:2]=2[CH:6]=1
Reactant: O=C(O)c1ccc(Cl)nc1
Reactant: COC(=O)c1sc(C)cc1N
Solvent: CO
Product: Cc1cc2nc3ccc(C(=O)O)cn3c(=O)c2s1
Temperature: 180 °C

Procedure:
A mixture of 1.7 g (0.01 mol) of 3-amino-5-methyl-2-thiophenecarboxylic acid, methyl ester (German Patent 1055007, April 16, 1959) and 1.6 g (0.01 mol) of 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company) is heated in an oil bath at 180° C. for two hours. The mixture is cooled, dissolved in hot methanol, cooled and 0.23 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid is collected; mp 338°-340° C. after recrystallization from methanol.
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][Cl:23])=[CH:18][CH:17]=1.[ClH:24].[OH-].[Na+]>C1(C)C=CC=CC=1>[ClH:23].[ClH:24].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:6]2([CH2:22][C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:15]=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:18][CH:17]=1
Reactant: ClCc1ccncc1
Reactant: COc1ccc2c(c1)Cc1ccccc1-2
Agent: Cl
Agent: [Na+]
Agent: [OH-]
Solvent: Cc1ccccc1
Product: COc1ccc2c(c1)C(Cc1ccncc1)(Cc1ccncc1)c1ccccc1-2

Procedure:
The title compound was prepared following the procedure of Example 5 from 1.8 g (9.2 mmole) of 2-methoxyfluorene, 3.0 g of 4-picolylchloride.HCl, 20 ml of 50% NaOH, 100 mg of cetyl Bu3PBr, and 30 ml of toluene by reaction at 50° for 6 hrs. The material was chramato-graphed to yield 1.6 g of product. δ: 3.37(s,4H), 3.89(s,3H), 6.52(broad,4H), 6.80(m,1H), 7.01(d,J=2.1 Hz,1H), 7.26(m,5H), 7.45(d,J=7.5 Hz,1H), 8.11(broad,4H).