4-Hydroxy-3-nitrobenzoic acid → Isopropyl Acetate

Participants

Reaction Steps

Intermediates: 5-(5-bromopentyl)-3-methylisoxazole and 2-bromo-4-(4,5-dihydro-2-oxazolyl)-6-nitrophenol. The latter, a bright yellow solid, was prepared by cyclization of 3-bromo-4-hydroxy-N-(2-hydroxyethyl)-5-nitrobenzamide, yellow solid, m.p. 163°-164° C. (from methanol-isopropyl acetate). The latter was in turn prepared by bromination of 4-hydroxy-3-nitrobenzoic acid to form 5-bromo-4-hydroxy-3-nitrobenzoic acid, m.p. 233°-234° C. (yellow solid from isopropyl acetate), esterification to the corresponding methyl ester, m.p. 128°-130° C. (yellow solid from carbon tetrachloride) and reaction of the latter with 2-hydroxyethylamine.

Provenance & Evidence