N-cyclopropyl-2-fluoro-6-nitroaniline → N1-cyclopropyl-6-fluorobenzene-1,2-diamine

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Reaction Steps

To a solution of N-cyclopropyl-2-fluoro-6-nitroaniline (650 mg, 3.31 mmol) in MeOH (15 mL) palladium 10 wt % on carbon (176 mg, 0.166 mmol) was added under N2. After flushing the flask with N2 for two minutes, the solution was stirred under a H2 balloon. After 6 h, the mixture was filtered through a celite pad rinsed with MeOH, and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using EtOAc:DCM (1:1) as eluent to give N1-cyclopropyl-6-fluorobenzene-1,2-diamine: LC-MS (ESI) m/z 167.1 [M+H]+.

Provenance & Evidence