Propionitrile → HCID 53389670, compound

HRID 1020862Notes

Reaction equation

HRID 1020862 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[C:5](\[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)/[CH3:6].[C:18](#[N:21])[CH2:19][CH3:20]>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:4]1[C:18]([CH2:19][CH3:20])=[N:21][N:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[C:5]=1[CH3:6])=[O:17]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 5993463HCID 5993463, compound

Product 1

HCID 53389670HCID 53389670, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-3-(4-nitrophenylamino)-but-2-enoic acid methylester (236.2 mg, 1.0 mmol, 1.0 equiv.) was stirred with Cu(OAc)2 (544.9 mg, 3.0 mmol, 3.0 equiv.) into propionitrile (3.0 ml, 41.9 mmol, 41.9 equiv.) for 21 hours at 120° C. The green solid obtained as raw product 100:0→90:10→0:100), whereby the pure product was obtained in the form of a slightly yellowish solid (188.3 mg, 0.65 mmol, 65%).

Workup

  1. customThe green solid obtained as raw product 100:0→90:10→0:100), whereby the pure product

Sources & evidence

ORD record
ord-c008f5bbcd434743b7208553b13f473e
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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