Hydrochloric Acid → HCID 87126409, compound

Participants

Reaction Conditions

Reaction Steps

2-(Benzyloxy)-4-[4-(methylsulfonyl)phenoxy]aniline (43.8 g) was suspended in a mixed solvent of acetonitrile(50 mL)-ethanol (400 mL), and concentrated hydrochloric acid (25 mL) was added at 10° C. Moreover, ethanol (100 mL) was added. Sodium nitrite (9.8 g) dissolved in water (16 mL) was added dropwise at −5 to 0° C., and the mixture was stirred at −5° C. for 30 min. To the reaction mixture was added water (100 mL), and the mixture was added dropwise to a mixture of ethyl 2-methyl-3-oxobutanoate (18.8 mL), potassium hydroxide (85%, 23 g), water (100 mL), and ethanol (100 mL) at −13 to −11° C. over 2 hr. The reaction mixture was stirred at −11° C. for 40 min, and the precipitated orange solid was collected by filtration. The obtained solid was washed with ethanol and diethyl ether to give the title compound (52.3 g, yield 91%) as orange crystals.

Provenance & Evidence