ChemInform Abstract: A Mild Chemospecific Reductive Dehalogenation of Ethylaminobenzamides with Lithium Aluminum Hydride.

✍ Scribed by James A. Hendrix; David W. Stefany

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199947078

✦ Synopsis

A Mild Chemospecific Reductive Dehalogenation of Ethylaminobenzamides with Lithium Aluminum Hydride.

-Secondary N-(2aminoethyl)benzamides substituted at the ortho-position of the phenyl ring with halogen are dehalogenated at this position by treatment with LiAlH 4 at room temperature. The p-iodo derivative (III) is also dehalogenated. A study of a series of other benzamides under the same conditions shows that the method only works well for secondary N-(2-aminoethyl)benzamides (amino: -NMe 2 , piperidino, morpholino) and fails for N-alkyl, N-(2-methoxyethyl) amides, amides with longer chains (three carbons or four carbons) between the amino and amide group, amides with a hindered amino group and for tertiary amides.