Hydroxylamine → 1-Heptyl-3-Hydroxyaminocarbonyl-4-Hydroxy-2(1H)-Quinolinone

Participants

Reaction Steps

A round-bottomed flask was charged with the product from step (1) (493 mg, 1.49 mmole), sodium methoxide (208 mg, 3.85 mmole), hydroxylamine (278 mg, 4.0 mmole) and methanol (10 mL). The reaction was stirred for 24 hrs and the precipitated product was collected by filtration, washed with water and dried in vacuo to give the title compound (40% yield). That the expected product was obtained was confirmed by the spectral data: M.S. (FAB): m/e 319 (M·+ +H); NMR (DMSO-d6): δ8.25 (1 H, d), 7.85 (1H, dd), 7.7 (1H, d), 7.45 (dd), 4.4 (2H, m, CH2N), 2.95 (br s, exchangeable protons), 1.8 (2H, m), 1.55 (8H, m), 0.95 (3H, t, CH3).

Provenance & Evidence