Acetonitrile → HCID 12595218, compound

HRID 1020865Notes

Reaction equation

HRID 1020865 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:16])[CH3:15]>CC([O-])=O.CC([O-])=O.[Cu+2].CC(OC)(C)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[C:14]([CH3:15])=[N:16][N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=1)=[O:13]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 300106HCID 300106, compound

Product 1

HCID 12595218HCID 12595218, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 18176222EtOAc MTBESolvent

Procedure

According to AVV A, 3-phenylamino acrylic acid methylester (197) (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 acetonitrile (3.0 ml, 57.1 mmol, 57.1 equiv.) for 22 hours at 110° C. The greenish solid obtained as raw product (242.4 mg) was purified by means of column chromatography (silica gel (50 g), pentane/MTBE 95:5→0:100, then MTBE/EtOAc 100:0→0:100), whereby the desired product was obtained in the form of a yellowish solid (35.1 mg, 0.16 mmol, 16%).

Workup

  1. customThe greenish solid obtained as raw product (242.4 mg)
  2. customwas purified by means of column chromatography (silica gel (50 g), pentane/MTBE 95:5→0:100

Sources & evidence

ORD record
ord-ac38686c9e0147a385fa23b7a420e078
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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