Preparation of methyl carbamates via a modified Hofmann rearrangement

✍ Scribed by Xicai Huang; Jeffrey W. Keillor

• Book ID: 104256089
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 154 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02341-6

✦ Synopsis

Treatment of a series ofpara-substituted aromatic and primary aliphatic carboxamides with NBS and NaOMe in methanol heated to reflux for ten minutes results in the conversion of the carboxamides to their corresponding primary amino methyl carbamates in nearly quantitative yields. The mild oxidative conditions of this modified Hofmann rearrangement are shown to be particularly useful for the preparation ofp-substituted anilines.