Hydroxyamine hydrochloride → HCID 73991942, compound

Participants

Reaction Steps

2-Methoxy-7,8-dihydro-5H-quinolin-6-one (246 mg, synthesized according to J. Org. Chem. 1991, 56 (15), 4636) was dissolved in ethanol/water 1:1 (14 ml) and sodium acetate (600 mg) and hydroxylamine hydrochloride (482 mg) was added. The resulting suspension was heated to reflux for 4 hours until TLC analysis confirmed complete consumption of the starting tetrahydroquinolinone. The reaction mixture was poured into a mixture of ice, water and 1N NaOH (pH>10) and the aqueous layer was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried and evaporated to give a crude product. This was purified by flash chromatography (gradient of ethyl acetate in hexanes, 20% to 50%) to give the desired product as a mixture of (E/Z)-isomers (232 mg) as a yellow solid. Mp: 124-126° C. MS (ISP): 193.1 (MH+).

Provenance & Evidence