Ammonia → 6-Chloro-3,4-dihydroisoquinolin-1(2H)-one
Reaction equation
C[O:2][C:3](=O)[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.N>>[Cl:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C:3](=[O:2])[NH:4][CH2:5][CH2:6]2Participants
3
Conditions
- Temperature
- 120 °C
Procedure
Under N2 protection, a mixture of [2-(3-chloro-phenyl)-ethyl]-carbamic acid methyl ester (5.0 g, 23.4 mmol) and PPA (polyphosphoric acid) (20 g) in a 250 mL round-bottom flask was vigorously stirred at 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was treated with ice-water and aqueous ammonia solution to adjust the pH to 8. Then, the mixture was then extracted with EtOAc, and the organic layer was washed with brine, dried over anhy. Na2SO4 and filtered. After removal of solvent under reduced pressure, the crude product obtained was further washed with ethyl ether to give title compound (1.66 g, 39%) as a white solid. MS: 182.0 (M+H+).