Acetic Acid → HCID 21440368, compound

Participants

Reaction Steps

To a cold (ice/water bath) vigorously stirred solution of crude (2-Chloro-4-nitrophenyl)-carbamic acid ethyl ester (5.8 g, 21.8 mmol) in tetrahydrofuran (THF) (100 mL) and acetic acid (12 mL) zinc powder (20 g) was added by small portions maintaining the temperature below 40° C. The mixture was allowed to warm slowly to room temperature and after reaction completion (1 hour) it was filtered via a plug of SiO2 (20 g) with ethyl acetate as an eluent. The obtained solution was evaporated in vacuo and the crude yellow solid residue (4.9 g) was purified by precipitation from tetrahydrofuran (THF)/heptane to give 3.00 g of the title compound as pale yellow solid, yield 56%. LC/MS (m/z) 214, 216 (M+); RT=1.18, (UV, ELSD) 86%, 97%. 1H NMR (DMSO-d6): 1.18 (br. t, 3H), 4.02 (q, 2H), 5.29 (s, 2H, NH2), 6.45 (dd, 1H), 6.61 (d, 1H), 6.98 (br. d, 1H), 8.52 (br. s, NHCO).

Provenance & Evidence