Hydrochloric Acid → 3-nitro-N-phenylpyridin-4-amine

Participants

Reaction Steps

A solution of 4-chloro-3-nitropyridine (II: R′=4-aza, halogen=Cl) (3.22 g, 0.020 mol), aniline (III: R1′=H) (1.85 mL, 0.020 mol) and conc. HCl (0.17 mL, 0.02 mol) in 1:1 water/2-methoxyethanol (40 mL) was refluxed for 18 hours, then concentrated to dryness. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic portion was worked up to give an oil which was chromatographed on silica gel. Petroleum ether eluted foreruns, while EtOAc/petroleum ether (1:1) gave 4-(N-phenylamino)-3-nitropyridine (VI: R′=4-aza, R1′=H) (2.02 g, 41%); mp (EtOAc/petroleum ether) 119° C.

Provenance & Evidence