Acetic Acid → HCID 58964483, compound

Participants

Reaction Steps

2.06 ml (4.12 mmol) of a 2M solution of diazomethyl-trimethyl-silane in hexane are added with slight cooling at 20° C. to a solution of 1.0 g (4.13 mmol) of 2-acetylamino-5-fluoro-4-nitro-benzoic acid in 15 ml of methanol and 35 ml of benzene. HPLC analysis after 15 minutes shows that there are still about 50% of the starting material present. Additional 2.4 ml (4.8 mmol) of the diazomethyl-trimethyl-silane solution are added. After standing for about 16 hours, no starting material can be detected by HPLC. 0.5 ml of glacial acetic acid are added and the reaction mixture is evaporated to dryness. Toluene is added and the mixture is again evaporated. The resulting residue is dissolved in refluxing ethyl acetate, hexane is added, the formed crystals are filtered, washed with hexane and dried at about 0.01 torr and 50° C. yielding 912 mg (86%) of 2-acetylamino-5-fluoro-4-nitro-benzoic acid methyl ester, m.p. 124-126° C.

Provenance & Evidence