Sodium Hydroxide → N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamide

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Reaction Steps

Sodium hydroxide (12.0 g, 300 mmol) in water (15 mL) was added slowly to a solution of piperonyl chloride (5.55 g, 30 mmol) and N,O-dimethylhydroxylamine hydrochloride (3.53 g, 36 mmol) in acetonitrile (200 mL). The mixture was stirred at room temperature for 0.5 h. Acetonitrile was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. Column chromatography on silica gel eluting with ethyl acetate:hexanes (30:70) gave 5.5 g (88%) of the title compound as a yellow oil. MS (ES+) m/z 210.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 1H), 7.26 (d, 1H, J=1.3 Hz), 6.86 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 3.61 (s, 3H), 3.38 (s, 3H).

Provenance & Evidence