3-chloro-N-phenylpropanamide → Hydrocarbostyril

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of AlCl3 (116.2 g, 0.87 mol) was added 3-chloro-N-phenylpropanamide (74-1; 40 g, 0.22 mol). Reaction mass was heated at 120° C. for 3 h. The reaction mixture was cooled to room temperature and diluted with ice cold water (500 mL) and washed with 1N aqueous hydrochloric acid solution (500 mL) slowly under cooling condition and extracted with ethyl acetate (4×200 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 stirred with n-pentane (250 mL) for 0.5 h and filtered with n-pentane (50 mL) to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.33 (bs, 1H), 7.26-7.15 (m, 2H), 7.00-6.97 (t, J=7.4 Hz, 1H), 6.79-6.77 (d, J=7.6 Hz, 1H), 2.99-2.95 (t, J=7.6 Hz, 2H), 2.66-2.63 (t, J=7.4 Hz, 2H). MS (M+1): 148.1.

Provenance & Evidence