Methyl chloroformate → N-Hydroxy-N-methyl-3-(3-phenoxyphenyl)prop-2-enamide

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Reaction Steps

Methyl chloroformate (2.6 ml) was added dropwise to a solution of m-phenoxycinnamic acid (8 g) and triethylamine (18.5 g) in tetrahydrofuran (60 ml) at 0°. A solution of N-methylhydroxylamine hydrochloride (5.6 g) in water (5 ml) was added, and the mixture was stirred for 2 hours. Isolation with ethyl acetate afforded 3-phenoxy-N-methylcinnamohydroxamic acid (ca. 4.3 g), m.pt. 124°-125° [from ethyl acetate/light petroleum (b.pt. 60°-80° C.)]. The m-Phenoxycinnamic acid used as starting material was prepared by condensation of m-phenoxybenzaldehyde with malonic acid in the presence of piperidine and pyridine.

Provenance & Evidence