Hydroxyamine hydrochloride → HCID 53675818, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 24 (0.50 g, 0.0015 mol), hydroxylamine hydrochloride (0.21 g, 0.0031 mol) and 4 Å molecular sieves were suspended in pyridine (10 ml) and heated at 60° C. for 14 h. A further amount of hydroxylamine hydrochloride (0.42 g, 0.0062 mol) was added and the reaction mixture heated under reflux for a further 24 h. The reaction mixture was diluted with ethyl acetate (30 ml) and filtered through hiflo. The mixture was washed with 1N hydrochloric acid (100 ml), the acid layer was back extracted with ethyl acetate (2×20 ml) and the combined organic layers were washed consecutively with water (20 ml), saturated sodium hydrogen carbonate solution (20 ml) and brine (20 ml), then dried (MgSO4), filtered, and concentrated in vacuo to give a white solid. This was recrystallised from ethanol/water to give a white crystalline solid; yield=278 mg. Mp=196°-198° C. Found: C, 62.93; H, 4.37; N, 8.10. C18H15ClN2O3 requires C, 63.07; H, 4.41; N, 8.17. δ (360 MHz, DMSO-d6), 1.60 (3H, s, CH3), 4.06 (2H, s, OCH2), 7.28 (1H, dd, J=8.6 and 2.1 Hz, 6-H), 7.32-7.48 (6H, m, aromatics), 7.78 (1H, d, J=8.7 Hz, 5-H), 10.88 (1H, s, NOH), 11.92 (1H, s, br, NH). MS (CI) m/z=343 [MH]+.

Provenance & Evidence