An improved synthesis of 3-hydroxymethylantipyrine using antipyrine as starting material. 1986

W Buijs, and B van Meeteren-Wälchli, and D D Breimer, and A van der Gen

A partly new synthesis of 3-hydroxymethylantipyrine, an important metabolite of antipyrine in man and therefore frequently used as a reference substance, is described. The use of tri-n-butyltin hydride to reduce the vinyl bromide system in 3-hydroxymethyl-4-bromoantipyrine is the main improvement, since it enables the isolation of salt-free 3-hydroxymethylantipyrine in an almost quantitative yield.

UI MeSH Term Description Entries
D000983 Antipyrine An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29) Phenazone,Anodynin,Pyramidone
D014220 Trialkyltin Compounds Organometallic compounds which contain tin and three alkyl groups. Compounds, Trialkyltin

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