2,4-Dichloro-3-ethyl-6-nitrophenol → Phenol, 6-amino-2,4-dichloro-3-ethyl-, hydrochloride (1:1)

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-3-ethyl-6-nitrophenol (20 g, 98.4% purity) was dissolved in methanol (80 g), to which Raney nickel (0.8 g) and activated carbon (0.2 g) were added and into which hydrogen gas was introduced at a hydrogen pressure of 4 kg/cm2 at 40° to 45° C. until no absorption of hydrogen gas was found. After completion of the reaction, Raney nickel was removed in air, and hydrochloric acid (17.7 g) was added dropwise, and the reaction mixture was cooled to 20° C., which resulted in a deposition of crystals. The deposited crystals were washed with acetone (28 g) and dried, which afforded 16.2 g of 2,4-dichloro-3-ethyl-6-aminophenol hydrochloride. To this hydrochloride salt, the above distillation-purified acid chloride compound (23.4 g) was added in air, and the mixture was heated under reflux in acetonitrile (162 g) for 2 hours. After completion of the reaction, the reaction mixture was cooled to 10° C., and the deposited crystals were filtered, washed with acetonitrile (16 g) and dried, which afforded 30.1 g of the desired amide compound (m.p., 145°-146° C., 98.9% purity). These crystals were recrystallized from acetonitrile (150 g), and 28.2 g of crystals having a purity of 99.3% were obtained (82.2% yield in the amidation step).

Provenance & Evidence