Formaldehyde → 1-(7-Chloro-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethan-1-one

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Reaction Steps

To a mixture of concentrated sulfuric acid (40 mL) and acetic acid (60 mL), N-[2-(4-chlorophenyl)ethyl]-2,2,2-trifluoroacetamide (14.2 g) and paraformaldehyde (2.79 g) were added sequentially and stirred overnight under an argon atmosphere. The reaction mixture was added to ice-cold water, extracted with ethyl acetate, and then washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 7-chloro-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (13.7 g) as a light-yellow solid.

Provenance & Evidence