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Author: Subject: Clortermine synthesis question
Illegal Parkinson
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[*] posted on 29-5-2015 at 08:08
Clortermine synthesis question

US 3415937

1. Grignard reagent of o,a-dichlorotoluene is reacted with acetone.
2. Tetrtiary alcohol of last step is reacted with NaCN in glacial HOAc.
3. Product of the last step (presumably nitrile) is boiled in mineral acid.

I know Hofmann rearrangement can convert an amide to an amine in base and Br2.

How exactly is the above reaction get a cyanide functional group into an amine just by boiling it in acid?

Obviously pedantic point i mean alkaloid amine not ammonia by amide hydrolysis.

[Edited on 29-5-2015 by Illegal Parkinson]
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