Water → HCID 66976085, compound

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:6].[H-].[Na+].O>C1COCC1>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Procedure

To a solution of ethyl 2-[(4-chlorobutanoyl)amino]benzoate (8.03 g) in THF (120 ml) was added 60% sodium hydride (2.14 g) at 0° C., and the mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into water, and the mixture was partitioned twice with ethyl acetate. The organic layers were combined, and the mixture was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.3 g).