Trifluoroacetic acid → Methyl 2-(4-chloro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Participants

Reaction Steps

To a solution of methyl 2-(4-chloro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (8.2 g, 21 mmol) in dichloromethane (150 mL), which was cooled to −10° C. under a nitrogen atmosphere, was added triethylsilane (7.08 g, 60.9 mmol) and trifluoroacetic acid (9.82 g, 86.1 mmol). The resulting reaction mixture was stirred overnight at room temperature. The mixture was neutralized with 20 g of Sodium bicarbonate. The solid was filtered and the filtrate was evaporated to remove the solvent. The residue was dissolved in methanol, and insoluble solid was the crude product (3.0 g). The filtrate was purified on silica gel to afford 170 mg of methyl 2-(4-chloro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate.

Provenance & Evidence