Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[OH:16])[CH:4]=[CH2:5].[C:17]1([OH:23])C=CC=[CH:19][CH:18]=1.S(C1C=CC(C)=CC=1)(OC[C@@H]1OC1)(=O)=O>>[CH2:3]([O:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[O:16][CH2:19][CH:18]1[CH2:17][O:23]1)[CH:4]=[CH2:5]
Reactant: Oc1ccccc1
Reactant: C=CCOc1cc([N+](=O)[O-])ccc1O
Agent: Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1
Agent: [H-]
Agent: [Na+]
Product: C=CCOc1cc([N+](=O)[O-])ccc1OCC1CO1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
20 g (0.50 mole) of 60% NaH/mineral oil was placed in a two liter flask and washed with 500 ml of hexane. 1 L of DMF was added, followed by 77 g (0.40 mole) of the 2-allyloxy-4-nitrophenol prepared in the previous step. Addition of the phenol was performed in portions under argon. After stirring the mixture for 30 minutes at room temperature under argon, 108 g (0.48 moles) of (R)-glycidyl tosylate was added and the mixture heated at 70°-75° C. under nitrogen overnight. Upon cooling, the DMF was removed in vacuum and replaced with one liter of methylene chloride. This was washed with 500 ml portions of 2N HCl, saturated sodium bicarbonate and saturated brine and dried over sodium sulfate. The mixture was filtered, concentrated to an oil in vacuum and column chromatographed on silica gel using 1:1 hexane/methylene chloride as eluant. This gave 43 g of product contaminated with traces of the two starting materials, followed by 21 g of pure product as a pale yellow solid. The impure material was recrystallized from 1.2 L of 10% ethyl acetate/hexane to give 34 g of pure (homogeneous on silica gel tlc with 1:1 hexane/methylene chloride) (R)-2-(2-allyloxy-4-nitrophenoxymethyl)-oxirane (m.p. 64° C).
Reaction SMILES: C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:14])=[O:11])=[CH:6][C:5]=1[Cl:25].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:25][C:5]1[CH:6]=[C:7]([C:10]([NH:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:26])=[O:2]
Reactant: COC(=O)c1ccc(C(=O)N[C@H](C)c2cccc3ccccc23)cc1Cl
Agent: [Li+]
Agent: [OH-]
Solvent: CO
Solvent: C1CCOC1
Solvent: O
Product: C[C@@H](NC(=O)c1ccc(C(=O)O)c(Cl)c1)c1cccc2ccccc12
Temperature: 25 °C
Reaction time: 4 h
Yield: 80.5 %

Procedure:
To a solution of (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid methyl ester (Example 82; 3.00 g, ˜8.5 mmol) in tetrahydrofuran/methanol/water (3:1:1; 20 mL) was added lithium hydroxide monohydrate (1.43 g, 34 mmol). The mixture was allowed to stir at room temperature for 4 h and then concentrated in vacuo to remove tetrahydrofuran and methanol. The concentrate was diluted with water and extracted with three portions of ethyl acetate. The organic extracts were discarded and the aqueous layer was acidified with 1N hydrochloric acid solution. Ethyl acetate was added and the resulting colorless solid was recovered by filtration and washed with ethyl acetate. The layers in the filtrate were separated and the organic phase was dried (MgSO4), filtered and concentrated. The resulting residue was combined with the previously recovered solid to give (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid (2.42 g, 84% yield).
Reaction SMILES: [Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br.Br[CH:12]([C:14]1[CH:15]=[C:16]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[CH:17]=[C:18]2[C:23]=1[O:22][C:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:20][C:19]2=[O:30])[CH3:13]>>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:12]([C:14]1[CH:15]=[C:16]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[CH:17]=[C:18]2[C:23]=1[O:22][C:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:20][C:19]2=[O:30])[CH3:13]
Reactant: Nc1cccc(Cl)c1Cl
Reactant: CC(Br)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12
Agent: Br
Product: CC(Nc1cccc(Cl)c1Cl)c1cc(C(=O)N(C)C)cc2c(=O)cc(N3CCOCC3)oc12
Yield: 52 %

Procedure:
2,3-dichloroaniline (0.097 mL, 0.82 mmol) was reacted with 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (0.1 g, 0.20 mmol) using an analogous procedure to the one described in Example 3.03 to give 8-(1-(2,3-dichlorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (51 mg, 51%) as a white solid. Mass Spectrum: M+H+ 490.