Propionitrile → HCID 68225677, compound

HRID 1020860Notes

Reaction equation

HRID 1020860 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]([O:14][CH2:15][CH3:16])=[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:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=2)[C:5]=1[CH3:6])=[O:17]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 67448671HCID 67448671, compound

Product 1

HCID 68225677HCID 68225677, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-3-(4-ethoxyphenylamino)-but-2-enoic acid methylester (235.3 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 24 hours at 120° C. The bluish-brown raw product (307.8 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→70:30→0:100), whereby the pure product was obtained in the form of a weak-yellow oil (254.7 mg, 0.88 mmol, 88%).

Workup

  1. customThe bluish-brown raw product (307.8 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→70:30→0:100), whereby the pure product

Sources & evidence

ORD record
ord-fe95dbfbf3044663bf798d148aef2a1c
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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