Propionitrile → HCID 12595218, compound

HRID 1020866Notes

Reaction equation

HRID 1020866 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14](#[N:17])[CH2:15]C>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:4]1[C:14]([CH3:15])=[N:17][N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=1)=[O:13]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 300106HCID 300106, compound

Product 1

HCID 12595218HCID 12595218, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, 3-phenylamino acrylic acid methylester (177.2 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 19 hours at 120° C. The orange-brown oily raw product (191.2 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→0:100), whereby the pure product was obtained in the form of a white solid (37.2 mg, 0.16 mmol, 16%).

Workup

  1. customThe orange-brown oily raw product (191.2 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→0:100), whereby the pure product

Sources & evidence

ORD record
ord-40ced5cfbd1c462f8e9605650faeefd4
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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