Oh O

Minocycline: Minocycline, 4,7-fcis(dimethylamino)-1,4,4a,5,5a,6,11,12 a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacencarboxamide (32.3.17), is synthesized from 6-dimethyl-tetracycline (32.3.11), which is synthesized as a result of the vital activity of S. aureofaciens, in which the mechanism of transferring methyl groups is disrupted, or from a common strain of the same microorganisms, but with the addition of compounds such as ethionin, D-norleucine or D-methionine to the medium for developing this actino-mycete, which are antimetabolytes of methionine, the primary donor of methyl groups in microbiological synthesis of tetracycline molecules. Hydrogenolysis of the aforementioned 6-demethyltetracycline (32.3.11) with hydrogen using a palladium on carbon catalyst gives 4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-napthacencarboxamide (32.3.12), which is nitrated at position 9 by potassium nitrate in aqueous hydrofluoric acid, which forms the nitro compound (32.3.13). This is reduced to the corresponding amino derivative (32.3.14) by hydrogen over platinum dioxide. The resulting aminophenyl compound (32.3.14) is then nitrated with nitric acid in the presence of sulfuric acid to make 7-nitro-9-amino-4-naphthacencarboxamide (32.3.15). This undergoes diazotization when reacted with butylnitrate in sulfuric acid, and the resulting diazo derivative (32.3.16) is reduced with hydrogen using a palladium on carbon catalyst. During this, the product is deazotized, while the nitro group is simultaneously reduced to an amino group, which undergoes exhaustive methylation by formaldehyde into minocycline (32.3.17) [231-237].


n(ch3)2 oh c4h3-ono/ h2so4

c4h3-ono/ h2so4

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