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How is the hydrolysis of amides done in a lab?

The answer, as with so much chemistry, is it depends. What substrate are you hydrolysing, is it a primary, secondary or tertiary amide? What else is in the molecule that you want to preserve? Both a …
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4 votes
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Gabriel Phthalamide Reaction

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. …
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2 votes

Reduction of amides with lithium aluminium hydride

Note: the pKa of primary amides is in the 22-25 range so not close to alcohols. …
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12 votes
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Can a cyclic amine form an amide?

The heterocycle in this question is indole and is aromatic. This means that the N lone pair is delocalised and not readily available for nucleophilic attack. Think of it as similar in reactivity to a …
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3 votes
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Why is S-alanine acetylated in the synthesis of S-cathinone?

The treatment of N-acetyl-S-alanine with PCl5 gives the acid chloride of the carboxylic acid and converts the N-acetyl group to the imidoyl chloride. This species undergoes classical F-C acylation wit …
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10 votes
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Can I synthesize an Amide simply by heating an amine and a carboxylic acid (with a vacuum pu...

Borate Esters: Simple Catalysts for the Sustainable Synthesis of Complex Amides. Sci. Adv. 2017, 3 (9), e1701028. DOI: 10.1126/sciadv.1701028. …
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4 votes
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What is the role of magnesium nitride in ammosamide B synthesis?

$\ce{Mg3N2}$ is magnesium nitride. It reacts with $\ce{MeOH}$ to generate magnesium methoxide and ammonia according to online report by Buske [1]. The $\ce{NH3}$ thus generated is acting as nucleophil …
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What is the balanced equation of BH3/THF with an amide to form an amine?

The reduction of secondary amides with BH3 requires 3 equivalents, mechanism shown below image sourced from here. The borane becomes HB=O which may transform further depending on work up. …
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