Hydroxyamine hydrochloride → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

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Reaction Steps

To a solution of hydroxylamine hydrochloride (29 mg, 0.416 mmol) in methanol (1.0 mL) was added solid NaHCO3 (37 mg, 0.437 mmol). After stirring 15 minutes at RT 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone (52 mg, 0.104 mmol) (INTERMEDIATE 73) was added. After stirring 18 hours the solution was concentrated. The residue was suspended in DCM and the solid filtered. The filtrate solution was concentrated and the residue purified by preparative thin layer chromatography using 5% MeOH in DCM as the eluent to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data 1.53 (m, 2H), 1.87 (dt, 1H, J=5.4, 14.2 Hz), 1.98 (m, 2H), 2.19 (m, 1H), 2.57 (brd, 1H, J=14.4 Hz), 2.64 (m, 1H), 3.38 (brd, 1H, J=15.2 Hz).

Provenance & Evidence