Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [H-].[Na+].[OH:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=1.Cl[C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)=[O:26].O>CN(C)C=O>[CH3:33][N:30]1[CH2:31][CH2:32][N:27]([C:25]([O:13][CH:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4](=[O:3])[N:5]2[C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[O:26])[CH2:28][CH2:29]1
Reactant: CN1CCN(C(=O)Cl)CC1
Reactant: O=C1c2ccccc2C(O)N1c1ccc2ncccc2n1
Agent: [H-]
Agent: [Na+]
Solvent: O
Solvent: CN(C)C=O
Product: CN1CCN(C(=O)OC2c3ccccc3C(=O)N2c2ccc3ncccc3n2)CC1
Temperature: 13 °C
Reaction time: 4 h
Yield: 56 %

Procedure:
A suspension of sodium hydride (50% dispersion in mineral oil) (1.46 g.) in anhydrous dimethylformamide (80 cc.) is added to a suspension of 3-hydroxy-2-(1,5-naphthyridin-2-yl)isoindolin-1-one (7 g.) in anhydrous dimethylformamide (410 cc.). When the evolution of gas has ceased, a solution of 1-chlorocarbonyl-4-methyl-piperazine (4.6 g.) in anhydrous dimethylformamide (25 cc.) is added dropwise. After stirring for 4 hours, the reaction mixture is poured into water (3,000 cc.) cooled to 13° C. The precipitate is filtered off, washed with water (75 cc.) and then dried to yield 3-(4-methylpiperazin-1-yl)carbonyloxy-2-(1,5-naphthyridin-2-yl) isoindolin-1-one (5.7 g.) melting at 170°-171° C. After recrystallisation from acetonitrile (50 cc.), the products melts at 173° C.