Thionyl Chloride → HCID 69217114, compound

Participants

Reaction Steps

To a mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (1-hydroxymethyl-3-methylbutyl)amide (b) (30.0 mg, 0.075 mmol) in DCM (8.0 mL) was added thionyl chloride (31.0 gL, 0.40 mmol) at rt. The reaction was stirred for 0.5 h at rt, cooled to 0° C., quenched with a cold solution of NaOH (1 N), and extracted with DCM (3×10 mL). The solvent was then removed in vacuo to provide 6-chloro-3-(4-isobutyl-4,5-dihydro-oxazol-2-yl)-4-phenyl-1H-quinolin-2-one (c) (25 mg, 87%). 1H NMR (CDCl3): δ 12.60 (b s, 1 H), 7.55-7.35 (m, 7 H); 7.20 (d, 1 H), 4.40 (t, 1 H), 4.30-4.20 (m, 1 H), 3.7 (t, 1 H), 1.60-1.50 (m, 1 H), 1.20-1.00 (m, 2 H), 0.80(dd, 6 H). MS: 381.3 (M+H).

Provenance & Evidence