Aniline → 3-chloro-N-phenylpropanamide

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To a stirred solution of aniline (40 g, 0.429 mol) in dichloromethane (500 mL) cooled at 0° C., was added 3-chloropropanoyl chloride (49.1 mL, 0.515 mol) drop wise with constant stirring. Reaction mass was allowed to stir at room temperature for 2 h. The reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (4×500 mL). The combined organic layer was washed with saturated sodium bicarbonate solution, saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.01 (s, 1H), 7.58-7.56 (d, J=8 Hz, 2H), 7.30-7.26 (t, J=8 Hz, 2H), 7.05-7.01 (t, J=7.6 Hz, 1H), 3.88-3.85 (t, J=6.4 Hz, 2H), 2.82-2.81 (t, J=6.0 Hz, 2H). MS (M+1): 184.1.

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