Acetic Acid → HCID 86664199, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of hydroxylamine hydrochloride (2.0 g, 29 mmol) in methanol (10 mL) was heated at 90° C. under a dry nitrogen atmosphere until homogeneous. To this heated solution was added a solution of potassium hydroxide (2.85 g, 50.8 mmol) in methanol (6 mL). A precipitate formed on mixing. After heating at 90° C. for 30 minutes, the mixture was cooled to rt and the solids were allowed to settle. The resulting solution was assumed to contain 1.7 M hydroxylamine.potassium salt and was carefully removed by syringe to exclude solids. An aliquot of the above solution (2.79 mL, 4.74 mmol) was added to a solution of methyl 3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.11 g, 0.47 mmol) in methanol (1 mL) and DMF (2 mL). After stirring for 4 h at rt, excess reagent was quenched by the addition of acetic acid (0.27 mL, 4.74 mmol). The mixture was concentrated to dryness and the residue was twice co-evaporated with toluene. The crude product was purified by preparative HPLC to afford N-hydroxy-3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxamide (21 mg, 19%). LC-MS: (FA) ES+ 236; 1H NMR (400 MHz, DMSO) δ 10.87 (s, 2H), 7.95 (d, J=8.2 Hz, 1H), 7.56 (s, 1H), 7.48 (dd, J=8.2, 1.1 Hz, 1H), 3.25 (s, 3H).

Provenance & Evidence