3-chloro-N-(2-fluorophenyl)propanamide → 8-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred aluminum chloride (26.53 g, 0.199 mol) was added 3-chloro-N-(2-fluorophenyl) propanamide (109-1; 10.0 g, 0.0497 mol). Reaction mass was heated 120° C. and stirred for 5 h. Then reaction mixture was cooled to room temperature and diluted with ice cold water (200 mL) and washed with 17% aqueous hydrochloric acid solution (50 mL) slowly under cooling condition and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was purified by silica gel column chromatography to obtain the title compound. MS (M+1): 166.1.

Provenance & Evidence