Phosphorus oxychloride → 4-Chloro-1-(3,4-dimethoxy-phenyl)-6-oxo-1,6-dihydro-pyridazine-3-carbonitrile

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Reaction Steps

The starting amide (30) (190 mg) was dissolved in 1 ml of CH3CN, treated with 1 ml of phosphorus oxychloride, and heated to reflux. After 18-20 hours the reaction was complete by HPLC. The reaction mixture was poured into ice and stirred for one hour. The product was extracted with ethyl acetate, the organic phase dried over magnesium sulfate, filtered, and concentrated to dryness. This material was then purified by normal phase column SiO2 chromatography affording 90 mg of desired nitrile chloride (31) as a solid. MS+: m/e=292.0 (M+H), 1H-NMR (500 MHz, MeOH-d4): d 7.40 (s, 1H), 7.18 (s, 1H), 7.12 (d, 1H), 7.08 (d, 1H), 3.90 (s, 3H), 3.85 (s, 3H), ppm.

Provenance & Evidence