Use of 4-substituted 2-butanones to prepare nabumetone

US5600009A · kind A · utility

Assignee

• Hoechst Celanese Corporation · US

Inventors

• John F. Fritch · Port Aransas, US
• Mohammad Aslam · Port Aransas, US
• Dora E. Rios · Port Aransas, US
• Joel C. Smith · Port Aransas, US

Key dates

• Filing date: Apr 9, 1996
• Grant date: Feb 4, 1997
• Expiry date: Apr 9, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C45/71
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.