Methanol → HCID 21936644, compound

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+].CO>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([OH:29])[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Procedure

To a solution of 1-(3-nitrophenyl)-3-[3-oxo-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (1.07 g, 2.7 mmol; prepared in Example 17) in dichloromethane (50 ml) was added sodium borohydride, and the mixture was admixed dropwise with methanol (30 ml) gradually while the reaction was monitored by TLC. After completion of the reaction, the mixture was evaporated, admixed with water, and filtered to give a solid which was dried. Recrystallization from DMF yielded 1-(3-nitrophenyl)-3-[3-hydroxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (770 mg, 71%; mp 235–236° C./DMF).