Benzonitrile → HCID 53389672, compound

HRID 1020864Notes

Reaction equation

HRID 1020864 reaction equation
[CH2:1]([O:3][C:4](=[O:18])/[CH:5]=[C:6](\[NH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17])/[CH3:7])[CH3:2].[C:19](#[N:26])[C:20]1C=CC=C[CH:21]=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([O:3][C:4]([C:5]1[C:19]([CH2:20][CH3:21])=[N:26][N:8]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:6]=1[CH3:7])=[O:18])[CH3:2]

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 62707354HCID 62707354, compound

Product 1

HCID 53389672HCID 53389672, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-3-(2,4,6-trimethylphenylamino)-but-2-enoic acid ethylester (247.3 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 oil obtained as raw product (524.3 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→0:100). The product was obtained in the form of a white solid (289.4 mg, 0.83 mmol, 83%).

Workup

  1. customThe brown oil obtained as raw product (524.3 mg)
  2. customwas purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→0:100)

Sources & evidence

ORD record
ord-ed73423bfc2d445e9faf8aebe40e7f7c
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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