Phosphorus oxychloride → N-(4-chloro-3-cyano-6-methoxy-7-quinolinyl)acetamide

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Reaction Conditions

Reaction Steps

An amount of 10 g (0.039 mol) of N-(3-cyano-6-methoxy-4-oxo-1,4-dihydro-7-quinolinyl)acetamide was subsequently stirred in 29 mL (0.31 mol) of phosphorus oxychloride, heated at 100° C. for 0.5 hours, and cooled to 0° C. To this was slowly added a saturated solution of sodium bicarbonate and ethyl acetate. After separation of the layers, the organic layer was washed with saturated brine, dried over sodium sulfate, and evaporated to give a brown solid (9.8 g, 73% yield), mp 230-235° C.; 1H NMR (DMSO-d6) δ 9.77 (s, 11-1), 8.98 (s, 1H), 8.94 (s, 1H), 7.50 (s, 1H), 4.11 (s, 3H), 2.25 (s, 3H); HRMS (EI) m/z 275.0466 (M+1). Analysis for C13H10ClN3O2.0.75H2O: Found: C, 53.99; H, 3.83; N, 14.53. Calcd: C, 53.62; H, 3.68; N, 14.98.

Provenance & Evidence