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

Participants

Reaction Steps

Treat a solution of 3,3-dimethylcyclobutylcarboxylic acid (0.500 g, 3.90 mmol) and oxalyl chloride (0.512 mL, 5.85 mmol) in DCM (30 mL) with catalytic DMF (1 drop), stir at RT for 4 h, concentrate to dryness, add additional DCM and concentrate to dryness again. Dissolve the residue in THF (10 mL), add drop-wise to a solution of NH4OH (2 mL, 51.4 mmol) in THF (20 mL), and stir at RT overnight. Extract with EtOAc (2×), wash the combined organics with brine, dry over MgSO4 and concentrate to dryness to afford the title compound (440 mg, 89%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.07 (s, 1H); 6.63 (s, 1H); 2.86 (m, 1H); 1.85 (m, 2H); 1.74 (m, 2H); 1.10 (s, 3H); 1.00 (s, 3H); MS(ESI) m/z: 128.2 (M+H+).

Provenance & Evidence