Dimethylformamide dimethyl acetal → (4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone

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Reaction Conditions

Reaction Steps

A N,N-dimethylformamide (1 mL) solution containing 1,4-dihydro-3(2H)-isoquinolinone (300 mg, 2.04 mmol) and N,N-dimethylformamide dimethylacetal (0.65 mL, 4.89 mmol) is heated at 100° C. for 2.5 hours. After removing the solvents, the residue is washed with ether, water and ether to give 88 mg of the product as a pink solid. The filtrate is evaporated to dryness, and the residue is treated with ether, water and ether to give 105 mg of a second crop of the product with a total yield of 47% (193 mg); MS (ESI) m/z 203.2 (M+1). Ref: Chemistry of Heterocyclic compd. 370-374 (1981).

Provenance & Evidence