Water → 4-Aminocinnamonitrile

HRID 596139Notes

Reaction equation

HRID 596139 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=1)([O-])=O.O>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]#[N:11])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 962WaterHCID 34056p-Nitrocinnamonitrile

Product 1

HCID 545249384-AminocinnamonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 120 parts of acrylonitrile and 1000 parts of acetone is introduced into the solution of the diazo derivative obtained from 276 parts of p-nitroaniline. Then, 40 parts of cupric chloride crystallised with 2 molecules of water are added and the mixture is stirred vigorously. The evolution of nitrogen is exothermic and the temperature should be kept at 30°-32° C. by means of a cooling bath. When the diazonium chloride has disappeared (6 hours), yellow leaflets melting at 108° C. are filtered off. After recrystallisation from methanol, one obtains 330 parts of 2-chloro-3-(4-nitrophenyl) propionitrile which melts at 112° C. This product is then dehydrohalogenated by means of 200 parts of crystallised sodium acetate in a mixture of 340 parts of water and 800 parts of ethyl alcohol. The mixture is refluxed for 12 hours and 225 parts of 4-nitrocinnamonitrile are isolated in the cold. Melting point: 202° C. The 4-nitrocinnamonitrile thus obained is then reduced by the Bechamp method in 2000 parts of water and 800 parts of ethyl alcohol. The 4-aminocinnamonitrile is obtained which melts at 109°-110° C. Yield: 76%.

Sources & evidence

ORD record
ord-526fbfc58c3e4cc0bda9ff2a0e408c4a
Source dataset
uspto-grants-1977_03
Patent number
US04010151

Reaction notes

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