Ammonia → 2-Naphthalenecarboxamide, 5,6-dihydro-7-(1H-imidazol-1-yl)-
Reaction equation
[N:1]1([C:6]2[CH2:7][CH2:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]([OH:18])=O)=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH3:19]>CN(C=O)C>[N:1]1([C:6]2[CH2:7][CH2:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16](=[O:18])[NH2:19])=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1,2-dihydro-3-(1-imidazolyl)-6-carboxy-naphthalene (500 mg) in DMF (10 ml) SOCl2 (2 ml) was added. Cooling in an ice bath, NH3 was passed through the reaction mixture, with stirring, for 5 hours. The reaction mixture was allowed to stand for 12 hours. The ammonium salt was filtered off and Et2O was added giving a precipitate which was chromatographed on silica gel with CHCl3 :CH3OH:CH3COOH (45:5:2.5) as eluant; 350 mg of 1,2-dihydro-3-(1-imidazolyl)-6-carbamoyl-naphthalene were obtained.