Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:25])[N:9]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.[H-].[Na+].[C:28](=O)([O:32]CC)[O:29][CH2:30][CH3:31].[CH3:36]I>O.O1CCCC1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([Cl:1])[CH:11]=3)[CH2:6][C:7]([CH3:36])([C:28]([O:29][CH2:30][CH3:31])=[O:32])[C:8]2=[O:25])[CH2:13][CH2:14]1)=[O:19])([CH3:22])([CH3:24])[CH3:23]
Reactant: CI
Reactant: CCOC(=O)OCC
Reactant: CC(C)(C)OC(=O)N1CCC(N2C(=O)CCc3ncc(Cl)cc32)CC1
Agent: [H-]
Agent: [Na+]
Solvent: O
Solvent: C1CCOC1
Product: CCOC(=O)C1(C)Cc2ncc(Cl)cc2N(C2CCN(C(=O)OC(C)(C)C)CC2)C1=O
Temperature: 70 °C
Reaction time: 4 h

Procedure:
To a tetrahydrofuran solution (10 ml) of tert-butyl 4-(7-chloro-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (Reference Example 9-3) (500 mg) were added at 0° C. sodium hydride (161 mg) and diethyl carbonate (0.66 ml). After the reaction solution was stirred at 70° C. for 4 hours, methyl iodide (0.171 ml) was added at 0° C., and stirred at room temperature for 6 hours. Water was added to the reaction solution at 0° C., and extracted with ethyl acetate. The collected organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford ethyl 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-7-chloro-3-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-carboxylate (286 mg).
Reaction SMILES: Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=O)=[C:7]([NH:15][C:16]([C:18]3[CH:19]=[N:20][O:21][C:22]=3[CH3:23])=[O:17])[C:6]=2[CH:24]=1.[CH2:25](N(CC)CC)C>O>[C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][CH:2]=[CH:24][C:6]=2[C:7]=1[NH:15][C:16](=[O:17])/[C:18](/[C:19]#[N:20])=[C:22](\[OH:21])/[CH3:23])(=[O:12])[CH3:25]
Reactant: CCN(CC)CC
Reactant: CCOC(=O)c1oc2ccc(Br)cc2c1NC(=O)c1cnoc1C
Solvent: O
Product: CC(=O)c1oc2ccccc2c1NC(=O)/C(C#N)=C(/C)O
Temperature: 68 °C
Yield: 449.5 %

Procedure:
To a solution (30 ml) of ethyl 5-bromo-3-[(5-methylisoxazole-4-carbonyl)amino]benzofurane-2-carboxylate (compound of Example 67 described below) (0.2 g, 1.8 mmol) produced according to Example 65 in water-free THF was added triethylamine (2.4 ml, 0.18 mmol), and the reaction mixture was heated at 68° C. for 6 hr and the solvent was evaporated. The residue was poured into ice water, and the mixture was acidified 30 with 5% aqueous hydrochloric acid solution and extracted with CHCl3. The extract was washed with saturated brine and dried. The solvent was evaporated. The residue was recrystallized from acetonitrile to give (Z)-N-(2-acetylbenzofuran-3-yl)-2-cyano-3-hydroxy-2-butenamide as colorless crystals (0.23 g, yield 22.6%).
Reaction SMILES: [C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.S(Cl)([Cl:12])=O>>[ClH:12].[C:1]([Cl:12])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1
Reactant: O=C(O)c1cccnc1
Reactant: O=S(Cl)Cl
Product: Cl
Product: O=C(Cl)c1cccnc1
Yield: 91 %

Procedure:
To nicotinic acid (41 g, 0.333 mol) at 0° C. was added thionyl chloride (115 ml, 1.58 mol) with stirring. The mixture was refluxed for one hour, and the white crystalline product was filtered and washed sparingly with dry benzene. Excess thionyl chloride was azeotroped off with dry benzene immediately before use. Yield 90% (53.97 g) of nicotinoyl chloride hydrochloride; NMR, IR identical with literature values.