Assisted hydrolysis of the nitrile group of 2-aminoadamantane-2-carbonitrile
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Attempts to hydrolyse the nitrile group of 2-aminoadamantane-2-carbonitrile by mineral acid or alkali have been unsuccessful. However, treatment of the aminonitrile with benzaldehyde in alkaline solution gives the benzal derivative of the α-aminoamide, readily hydrolysed to the α-aminoamide. Alternatively, benzoylation of the amino group followed by acid hydrolysis gives successively the α-benzamido acid and the α-amino acid. Possible mechanisms for these facilitated hydrolyses are advanced.
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2014 ◽
Vol 84
(10)
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pp. 2037-2042
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1979 ◽
Vol 36
(9)
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pp. 1134-1137
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1994 ◽
Vol 59
(8)
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pp. 1870-1878
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1970 ◽
Vol 50
(2)
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pp. 233-241
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1991 ◽
Vol 13
(3)
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pp. 93-95
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1965 ◽
Vol 18
(6)
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pp. 1227
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2016 ◽
Vol 202
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pp. 231-237
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