Aniline → Methyl 4-amino-3-fluoro-5-nitro-2-(phenylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

4-Amino-2,3-difluoro-5-nitrobenzoic acid methyl ester (23.48 g, 101.1 mmol) was suspended in xylenes (125 ml) and aniline (92 ml, 1011 mmol) was added. The reaction mixture was stirred at 125° C. for 16 hours under N2. The reaction mixture was cooled to room temperature and solids precipitated out of solution. The solids were collected by filtration and washed with xylenes and then diethyl ether. Recovered 22.22 g (72.78 mmol) of yellow solid which was pure desired product. The filtrate was concentrated under reduced pressure, redissolved in methylene chloride and flushed through a plug of silica gel eluting with methylene chloride. The desired fractions were concentrated under reduced pressure to give a brown solid which was triturated with diethyl ether to give 5.47 g (17.91 mmol) of yellow solid which was pure desired product. Combined product yield was 27.69 g (90%). MS APCI (−) m/z 304 (M−1) detected.

Provenance & Evidence