Process for preparation of benzylic amides

US10961213B2 · kind B2 · utility

Assignee

• BASF SE

Inventors

• Martin John McLaughlin · Bad Dürkheim, DE
• Karsten Koerber · Eppelheim, DE
• Birgit Gockel · Ludwigshafen, DE
• Devendra Vyas · Navi Mumbai, IN
• Arun Narine · Mannheim, DE

Key dates

• Filing date: Jan 16, 2018
• Grant date: Mar 30, 2021
• Expiry date: Jan 16, 2038

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D413/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a process for preparing benzylic amides of formula I wherein the variables have the meaning as defined in the description, by reductive amidation of a nitrile of formula II wherein the variables have the meanings given for formula I, with an activated carbonyl compound of formula III, and which nitrile is obtained by reaction of a compound of formula IV with a halogen compound of formula V, wherein X is a halogen atom, preferably bromo, which halogen compound V in turn is obtained by Sandmeyer reaction of an aniline derivative of formula VI novel compounds of formula I, and processes for preparing compounds of formula XII wherein the variables have the meaning as defined in the description by condensing compounds of formula I with compounds of formula X and subjecting the resulting α,β-unsaturated ketone of formula XI to a reaction with hydroxylamine to yield compounds of formula XII.