Methyl 3-(4-carboxy-2-nitrophenyl)propionate → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](OC)=[O:13])=[C:6]([N+:16]([O-])=O)[CH:5]=1)([OH:3])=[O:2].CO.[OH-].[Na+]>[Pd].CO>[C:1]([C:4]1[CH:5]=[C:6]2[C:7]([CH2:10][CH2:11][C:12](=[O:13])[NH:16]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

Procedure

5 Grams of methyl 3-(4-carboxy-2nitrophenyl)propionate, 8.87 ml of 2.226N-sodium hydroxide methanol solution, 100 ml of methanol and 1 g of 5%-Pd-C (50% in water) were well mixed together and this mixture was catalytically reduced at a normal temperature under a normal pressure. Then the catalyst was removed from the reaction mixture by filtration, and the pH of the filtrate was adjusted to about pH=1 by adding concentrated hydrochloric acid. The precipitated crystals were collected by filtration and recrystallized from methanol to obtain 3.62 g of 7-carboxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals.