Acetic Acid → HCID 13934949, compound

Participants

Reaction Steps

Acetaldehyde (0.3 ml, 0.007 mole) was added by pipet to a stirred solution of 2-[(2-chloro-4-hydrazinophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone hydrochloride (0.8 g, 0.0026 mole) and sodium cyanoborohydride (0.16 g, 0.0026 mole), in acetonitrile 25 ml). Glacial acetic acid (2 ml) was added, and the resulting mixture stirred at ambient temperature overnight. The reaction mixture was diluted with ether (200 ml) and washed with aqueous 0.5N sodium hydroxide (50 ml), then with water (2×50 ml). The ether layer was dried and then concentrated under reduced pressure to yield a yellow oil. The oil was chromatographed on silica gel, eluting with 30:70 ethyl acetate:heptane. Appropriate fractions were combined and concentrated under reduced pressure to yield 0.24 g of 2-[[2-chloro-4-(2,2-diethylhydrazinyl)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone as a white solid; m.p. 139°-141° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence