Process for selectively producing isosorbide-5-nitrate

US4297286A · kind A · utility

Assignee

• Sanol Schwarz-Monhein GmbH · DE

Inventors

• Klaus Sandrock · Langenfeld, DE
• Gunter Cordes · Leichlingen, DE

Key dates

• Filing date: Jan 24, 1980
• Grant date: Oct 27, 1981
• Expiry date: Jan 24, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention is related to a new process for selectively preparing isosorbide-5-nitrate (1.4-3.6-dianhydrosorbitol-5-nitrate) by subjecting isomannide (1.4-3.6-dianhydromannitol) in an organic solvent or an aqueous-organic reaction medium to reaction with the equivalent amount of an acid halogenide or the anhydride of a benzene or naphthalene sulfonic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen, of a perfluoro - lower alkane-sulfonic acid, of a lower alkanesulfonic acid or of a perfluoro - lower - alkanoic acid or with the equivalent amount of an acid halogenide of a carbamic acid or of sulphurous acid; subjecting the resulting isomannide-2-ester in the presence of a solvent and possibly with heating, to reaction with an alkali metal salt or an ammonium salt of a benzoic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen or of a lower alkanoic acid; converting the hydroxy group in the 5-position of the resulting isosorbide-2-ester into the nitric acid ester group in manners known per se by reaction with nitric acid; and subjecting the resulting isosorbide-2-ester-5-nitrate to selective hydrolysis and/or reesterification in an or…