Benzaldehyde → HCID 15675940, compound

Participants

Reaction Steps

A mixture of 6-amino-5-fluoro-4-methyl-2-benzoxazolone (Example 7 0.43 g, 2.40 mmoles) and benzaldehyde (0.26 g, 2.40 mmoles) in ethanol (2 ml) was refluxed for 2.5 hours. After cooling, the precipitated product was collected and washed with cold ethanol. To a mixture of the precipitate (0.63 g) and ethanol (8 ml) was added portionwise sodium borohydride (300 mg) at room temperature under stirring. Stirring continued for 15 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (1:4 by volume) to give the title compound (0.56 g). Recrystallization from methanol gave 0.44 g (68%) of the title compound as pale orange needles: m.p. 204°-206° C.

Provenance & Evidence