Abstract
THE synthesis of 7 : 8 : 4′ : 5′-tetramethoxy-3 : 4-dihydro-1 : 2-benzphenanthridone (I) has already been reported1. By treatment with phosphoryl chloride, the change —CO—NH— → —CCl=N— was readily effected (found in the product, m.p. 176–178°; C, 65.2; H, 4.9; Cl, 9.9 per cent), and this chloro-compound, in boiling p-cymene solution, may be reduced by hydrogen in the presence of palladized carbon and simultaneously dehydrogenated to the related tetramethoxybenzphenanthridine (—CCl=N— → —CH=N— and loss of 2H by dehydrogenation, —CH2.CH2— → —CH=CH—) (found in the product, m.p. 217–219°; C, 71.8, 72.1; H, 5.4, 5.3; N, 3.9 per cent).
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References
Bailey and Robinson, Nature, 164, 402 (1949).
Späth and Kuffner, Ber. deut. chem. Ges., 64, 2034 (1931).
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BAILEY, A., ROBINSON, R. & STAUNTON, R. Synthesis of a Reference Compound derived from Sanguinarine and Chelerythrine. Nature 165, 235 (1950). https://doi.org/10.1038/165235a0
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DOI: https://doi.org/10.1038/165235a0
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