Ammonia → 1-Phenylcyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.225 mL, 3.08 mmol) was slowly added to a solution of 1-phenylcyclopropanecarboxylic acid (0.50 g, 3.08 mmol) in toluene (10 mL) and DMF (0.3 mL). The reaction was then heated at reflux for 2 hours, then cooled down to 23° C. and treated (slow addition) with a solution of ammonia (2M in methanol, 10 mL). The reaction was then stirred at 23° C. overnight. The reaction was then diluted with hydrochloric acid (1N) and extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (0.474 g, 95%) as a solid which was used as such in the next reaction. 1H NMR (400 MHz, CDCl3) δ: 1.11 (2H, q, J=3.79 Hz), 1.60-1.66 (2H, m), 5.34 (1H, br s), 5.91 (1H, br s), 7.31-7.41 (3H, m), 7.43-7.47 (2H, m). HPLC ret. time (Condition B): 1.225 min.

Provenance & Evidence