HCID 58216632, compound → 3-Hydroxy-6-methoxy-3,4-dihydro-1,5-naphthyridin-2(1H)-one

Reaction equation

[OH:1][CH:2]([CH2:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1)[C:3](OCC)=[O:4].[H][H]>CO.[Pd]>[OH:1][CH:2]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[NH:15][C:3]1=[O:4]

Participants

Procedure

A roundbottom flask was charged with a solution of ethyl 2-hydroxy-3-(6-methoxy-3-nitropyridin-2-yl)propanoate (37 mmol) in methanol (500 ml). To the mixture was added 10% palladium on carbon (3 g). The solution was shaken under 40 psi of hydrogen for 12 hours. The resulting solution was then allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The mixture was then filtered and the filtrate was diluted with 100 ml of water. Hydrochloric acid was added until the pH=5. The mixture was filtered and the filtrate was adjusted to pH=8 by the addition of sodium carbonate. The solids that formed were collected by filtration to afford the title compound.