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Communication | Regular issue | Vol 3, No. 6, 1975, pp.439-443
Published online, 1st January, 1970
DOI: 10.3987/R-1975-06-0439
Pschorr Reaction on 1-(2-Aminophenyl)-1,2,3,4-tetrahydro-2-methylisoquinoline

Tetsuji Kametani,* Shiroshi Shibuya, Ramamurthy Charubala, Manakkal S. Premila, and Bentwal R. Pai

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Diazotisation and Pschorr reaction of 6-amino-N-methyl-6,7-dimethoxy-1-(3,4-methylenedioxyphenyl)isoquinoline, gave besides the deaminated product, the corresponding 3,4-dihydroisoquinoline with N-demethylation and concomittant oxidation at the 1,2-position. 6-Amino-N-methyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)isoquinoline, under identical conditions gave, besides the deaminated product, a deep orange compound, which has been assigned the structure 3,4-dihydro-6,7,11,12-tetramethoxy-5-nitroazafluoranthene.