Hydrochloric Acid → 6-Chloro-3-methylquinolin-5-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-3-methyl-5-nitroquinoline (6.70 g, 30.1 mmol) in methanol (45 mL) was added iron powder (5.55 g, 99.3 mmol), followed by careful addition of a concentrated aqueous HCl solution (15.6 mL). The resulting reaction mixture was heated for 1 h at 50° C. and concentrated at reduced pressure using a rotary evaporator. The residue was dissolved in water and basified (pH=9) using a 33% aqueous ammonia solution. The resulting brown suspension was extracted twice with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford the title compound as a brown solid (4.92 g, 25.5 mmol, 85%). 1H NMR (400 MHz, CDCl3, 298 K): δ=8.75 (s, 1H), 7.93 (s, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 2.56 (s, 3H). MS (ES+): 193 (M(C10H935ClN2)+H)+.

Provenance & Evidence