Benzocaine → HCID 70495644, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), 3-formyl-benzonitrile (2.62 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 2-(3-cyano-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.0 g, 45%) as a white solid: MS (ESI) M+1=335.3.

Provenance & Evidence