Benzonitrile → HCID 53389671, compound

HRID 1020863Notes

Reaction equation

HRID 1020863 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:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:4]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:25][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 7505BenzonitrileHCID 5993463HCID 5993463, compound

Product 1

HCID 53389671HCID 53389671, compoundYield 75%

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 benzonitrile (3.0 ml, 29.4 mmol, 29.4 equiv.) for 14 hours at 120° C. The brown solid obtained as raw product (533.2 mg) was purified by means of column chromatography (silica gel (50 g), CH2Cl2/EtOAc 100:0→90:10→0:100), whereby the pure product was obtained in the form of a slightly yellowish solid (253.5 mg, 0.75 mmol, 75%).

Workup

  1. customThe brown solid obtained as raw product (533.2 mg)
  2. customwas purified by means of column chromatography (silica gel (50 g), CH2Cl2/EtOAc 100:0→90:10→0:100), whereby the pure product

Sources & evidence

ORD record
ord-4ae9a98673664c45b31ef4ba9ec0e027
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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