Hydrochloric Acid → HCID 86658613, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of cuprous chloride (90 mg, 0.91 mmol) in acetic acid (60 mL) was bubbled with sulfur dioxide gas for 6 h at room temperature. A mixture of methyl 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (992 mg, 3.20 mmol) in conc. hydrochloric acid (30 mL) and acetic acid (10 mL) was stirred for 1 hour. After cooling to −10° C., a solution of sodium nitrite (334 mg, 4.84 mmol) in water (7 mL) was added dropwise below −10° C. The resulting mixture was stirred for 1 h at −10° C. The prepared sulfur dioxide-salt solution was added to the solution above at −10° C. After addition, the mixture was stirred for 24 h at room temperature. The reaction mixture was quenched onto 100 g of crushed ice. The mixture was extracted with dichloromethane (40 mL, four times). The combined organic layers were washed with water (40 mL, twice), saturated aqueous Sodium bicarbonate solution (30 mL, twice), and saturated brine (40 mL) and dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, and the organic solvent was evaporated under reduced pressure to afford 1.0 g of methyl 2-(3-(chlorosulfonyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate. MS (ESI+APCI) M+1=394.

Provenance & Evidence