4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester → 3-Amino-4-(2-bromopyridin-4-ylamino)benzoic acid methyl ester

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Reaction Steps

4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester 3 (6 g; 17 mmol) was dissolved in MeOH (200 ml) and Raney-nickel (0.6 g; 4.5 mmol) was added and subsequently hydrogenated under an atmosphere of H2 for 3 h. LCMS showed full conversion and the reaction mixture was filtered through a bed of Celite to remove the catalyst. Thorough washing with MeOH followed by evaporation of the solvent under educed pressure gave 4 as a brown solid. Yield 3.2 g; 60%. The product identity was confirmed by NMR and LCMS and taken for the next step.

Provenance & Evidence