Ammonia methanol → 6-Bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=O)[O:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH3:22].CO>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:7])[NH:22][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-bromo-4-phenylisocoumarin-3-carboxylic acid (15 g) in methanol (100 ml) was added 12% ammonia-methanol solution (60 ml) and the mixture was stirred at room temperature for 24 hrs. The reaction mixture was concentrated, and 1N hydrochloric acid was added to the obtained residue. The mixture was extracted with ethyl acetate. The organic layer was dried and concentrated and 4N hydrochloric acid ethyl acetate solution (30 ml) was added to the obtained oily substance. The mixture was stirred at room temperature for 2 hrs. and the reaction mixture was concentrated. The obtained crystal was washed with water and dried under reduced pressure to give 6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid as colorless crystals.