Sodium Hydroxide → N-Hydroxy-3-(2-quinolinyl)propanamide

Participants

Reaction Steps

To a solution of methyl 3-(2-quinolinyl)propanoate (4) (0.111 g, 0.52 mmol) and hydroxylamine hydrochloride (0.144 g, 2.07 mmol) in methanol (3 ml), a solution of NaOH (0.165 g, 4.13 mmol) in water (0.5 ml) was added and the resulting mixture was stirred at room temperature for 30 minutes. The pH of the reaction medium was brought to 7 with saturated KH2PO4, the mixture was extracted with ethyl acetate (3×−15 ml), and the combined extracts were dried (Na2SO4). The solvent was evaporated under reduced pressure, the residue was washed with small amount of ethyl acetate and crystallized from acetonitrile to give the title compound (0.054 g, 48.1%). M.p. 159-160° C. 1H NMR (DMSO-d6, HMDSO), δ: 2.45-2.57 (m, 2H, overlapped with a signal of DMSO); 3.15 (t, J=7.2 Hz, 2H); 7.44 (d, J=8.4 Hz, 1H); 7.54 (ddd, J=8.2, 7.6, and 1.2 Hz, 1H); 7.71 (ddd, J=8.6, 7.0, and 1.4 Hz, 1H); 7.92 (d, J=8.6 Hz, 2H); 8.25 (d, J=8.4 Hz, 1H); 8.71 (s, 1H); 10.44 (s, 1H). HPLC analysis on Omnispher 5 C18: impurities ˜2.3% (column size 4.6×150 mm; mobile phase-5% acetonitrile+95% 0.1M phosphate buffer (pH 2.5); detector UV 230 nm; sample concentration 0.5 mg/ml; flow rate 1.5 ml/min). Anal. Calcd for C12H12N2O2 containing 2% of inorganic impurities: C, 65.32; H, 5.48; N, 12.70. Found, %: C, 65.42; H, 5.39; N, 12.43.

Provenance & Evidence