Can we use acid chloride in place of alkyl chloride in Gabriel Phthalamide Reaction?
Maybe it can be used as process to synthesize amides.
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1$\begingroup$ In practice, there's no reason to; you can just use ammonia. $\endgroup$– orthocresolCommented Feb 17, 2019 at 21:06
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$\begingroup$ @orthocresol I mean theoretically if it's a possibility. $\endgroup$– aniketsharma00411Commented Feb 17, 2019 at 21:07
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1 Answer
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NO, this is not a viable way to make amides.
Phthamide anion will react with acyl halides, but the problem arises with the second step, the removal of the phthalimido group. The usual conditions described here of hydrolysis with hydroxide or reaction with hydrazine will result in removal of the acyl group to reform phthalimide plus the carboxylic acid, in the case of OH- hydrolysis, or the acyl hydrazide if using hydrazine. This is because the acyl group is the more electrophilic site for the nucleophile.
