Benzocaine → HCID 70496998, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), 3-trifluoromethyl benzaldehyde (3.48 g, 20 mmol) and ytterbium(III) triflate hydrate (1.86 g, 3 mmol) in acetonitrile (150 mL) was cooled to 0° C. in a sealed reaction bottle. Then a cooled solution of isobutene (5.6 g, 100 mmol) was added into. The reaction mixture was heated to 90° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) to afford 4,4-dimethyl-2-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.0 g, 40%) as a white solid: MS (ESI) M+1=378.3.

Provenance & Evidence