Sodium Bicarbonate → 7-Amino-4-(2,4-dichloroanilino)-6-hydroxy-3-quinolinecarbonitrile

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Reaction Conditions

Reaction Steps

An amount of 200 mg (0.50 mmol) of N-[3-cyano-4-(2,4-dichloroanilino)-6-methoxy-7-quinolinyl]acetamide, was stirred with pyridine hydrochloride (1.4 g, 12.5 mmol), and heated at 200° C. for 2 hours. The mixture was cooled to room temperature, stilled with ethyl acetate and saturated sodium bicarbonate solution, and filtered. The layers were separated, and the organic layer was subsequently washed with saturated brine solution, dried over sodium sulfate, and evaporated to a yellow oil. Purification was carried out by preparative thin layer chromatography (5% methanol in ethyl acetate), to yield a yellow solid (52 mg, 30% yield), mp 265° C. decomp.; 1H NMR (DMSO-d6) δ 10.26 (bs, 1H), 8.93 (s, 1H), 8.34 (s, 1H), 7.66 (d, J=2 Hz, 1H), 7.35 (dd, J=9Hz, J=2Hz, 1H), 7.32 (s, 1H), 7.10 (d, J=9 Hz, 1H), 6.99 (s, 1H), 5.90 (s, 2H); HRMS (EI) m/z 344.0897 (M+1). Analysis for C16H10Cl2N4O.0.5CH3OH: Found: C, 54.43; H, 3.12; N, 15.34. Calcd: C, 54.74; H, 3.32; N, 15.48.

Provenance & Evidence