Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 87522359, compound

Participants

Reaction Steps

A mixture of Example 9B (11.9 g, 55.45 mmol), N,O-dimethylhydroxylamine hydrochloride (5.7 g, 58 mmol), 1-hydroxybenzotriazole hydrate (7.88 g, 53.8 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (11 g, 57.58 mmol) and diisopropylethyl amine (47.4 g, 63.9 mL, 370 mol) was stirred in DMF (400 mL) at ambient temperature overnight. The solution was diluted with water and extracted with ethyl acetate. The combined organic extract was washed with saturated sodium bicarbonate solution, 1N HCl, water, brine, dried over Na2SO4, filtered, and evaporated in vacuo. The resulting material was chromatographed (SiO2, 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) to leave the title compound (6.85 g, 48% yield). 1H NMR (300 MHz, CDCl3) δ ppm 7.39 (dd, J=7.12, 2.37 Hz, 1H), 7.10-7.21 (m, 2H), 6.71 (s, 1H), 3.69 (s, 3H), 3.28 (s, 3H), 2.10 (s, 3H). MS (DCI+) 258 (M+H).

Provenance & Evidence