Hydrochloric Acid → 2-(3-Nitro-phenylamino)-pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-bromonicotinaldehyde (2.54 g, 13.6 mmol; synthesized according to SYNTHETIC COMMUNICATIONS, 23(19): 2727–2730 (1993)), 3-nitroaniline (2.26 g, 1.2 eq.), palladium acetate (123 mg, 0.04 eq.), 1,3-bis(diphenyl-phosphino)propane (341 mg, 0.06 eq.), and cesium carbonate (6.22 g, 1.4 eq.) in toluene (30 ml) was stirred at 100° C. for 4 hours under nitrogen atmosphere, and cooled to room temperature, followed by addition of 10% hydrochloric acid (50 ml) and dichloromethane. The mixture was stirred for 1 hr, then diluted with water (50 ml), and extracted with dichloromethane. The extract was dried, and then evaporated. To the residue was added hexane to precipitate crystals, filtered off, washed with hexane, and dried under reduced pressure to afford 2-(3-nitrophenylamino)-nicotinaldehyde as a yellow powder (2.75 g, 74%).

Provenance & Evidence