Benzene → (1Z,2E)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]-2-[3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propenyl]isoquinoline

Beteiligte Stoffe

Reaktionsschritte

To a solution of 100 parts of 3-(3,4,5-trimethoxyphenyl)-2-propenoic acid in 1125 parts of benzene is added 22 parts of N,N-diethyl-1-propyne-1-amine. The resultant mixture is stirred for 2 hours, whereupon a solution of 75 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]isoquinoline [Ber. deut. chem. Ges., 55, 2889 (1922)] in 200 parts of pyridine is introduced. The mixture thus obtained is stirred and heated at 65° for 3 hours, then cooled, consecutively washed with water and aqueous 5% sodium bicarbonate, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and ether to give (1Z,2E)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methylene]-2-[3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propenyl]isoquinoline melting at 180°-183°.

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