Synthesis of ethambutol

Details Synthesis of ethambutol Synthesis of ethambutol

1974-08-01

1976-03-16

Sneed, Helen M. S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26050117, C07C 8900, C07C 8904, C07C 9104

Patent

active

039446182

ABSTRACT:
D-2-Amino-1-butanol, for the synthesis of ethambutol hydrochloride, d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride, is produced in high purity and good yields by the reaction of butene-1, a nitrile, preferably an excess of acetonitrile, and chlorine to form N-[1-(chloromethyl)propyl]acetimidoyl chloride which is hydrolyzed to dl-2-amino-1-butanol, which can be isolated as the hydrochloride, or free base, or a mixture, resolved with L(+)-tartaric acid and the d-2-amino-1-butanol reacted with ethylene dichloride and then hydrochloric acid to form ethambutol hydrochloride. A minimum of by-products which are conveniently split out permits the economical synthesis of a pharmaceutical grade product.

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