Ammonia → HCID 4532577, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of acetamide 168 (835 mg, 4.4 mmol) in 6 M HCl (50 mL) was stirred at 100° C. for 16 h. The suspension was cooled to 20° C., diluted with water (50 mL) and the pH adjusted to 8 with dilute aqueous NH3 solution. The mixture was extracted with DCM (3×50 mL), the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with 20% EtOAc/pet. ether, to give amine 169 (755 mg, 56%) as an orange solid: mp (EtOAc/pet. ether) 76-78° C.; 1H NMR δ 6.98 (d, J=8.4 Hz, 1H, H-4), 6.58 (d, J=8.4 Hz, 1H, H-3), 4.73 (br s, 2H, NH2), 2.76-2.81 (m, 2H, CH2), 2.65-2.69 (m, 2H, CH2), 1.69-1.78 (m, 2H, CH2). Anal. calcd for C10H12N2O2: C, 62.5; H, 6.3; N, 14.6. Found: C, 62.8; H, 6.1; N, 14.6%.

Provenance & Evidence