Ammonium Hydroxide → 3,3-Dimethylcyclobutane-1-carboxamide

Participants

Reaction Steps

A solution of 3,3-dimethylcyclobutane carboxylic acid (0.5 g, 3.90 mmol) and oxalyl chloride (0.512 mL, 5.85 mmol) in DCM (10 mL) was treated with DMF (1 drop) and stirred at RT for 2 h. The mixture was concentrated to dryness, treated with DCM (5 mL) and concentrated to dryness a second time. The crude acid chloride was dissolved in THF (5 mL), added drop-wise to a solution of NH4OH (˜15M, 3.80 mL, ˜57 mmol) in THF (5 mL), stirred for 30 min, diluted with brine and extracted with EtOAc (3×). The combined organics were dried over MgSO4 and evaporated to afford 3,3-dimethylcyclobutanecarboxamide (448 mg, 90%). 1H NMR (400 MHz, DMSO-d6): δ 7.07 (s, 1H), 6.64 (s, 1H), 2.86 (m, 1H), 1.86 (m, 2H), 1.75 (m, 2H), 1.10 (s, 3H), 1.00 (s, 3H).

Provenance & Evidence