Propionitrile → HCID 53389694, compound

HRID 1020871Notes

Reaction equation

HRID 1020871 reaction equation
[C:1]1([NH:7]/[C:8](/[CH3:13])=[CH:9]\[C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](#[N:17])[CH2:15][CH3:16]>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:15]([C:14]1[C:9]([C:10](=[O:12])[CH3:11])=[C:8]([CH3:13])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:17]=1)[CH3:16]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 57053294-Phenylamino-3-penten-2-one 97

Product 1

HCID 53389694HCID 53389694, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-4-phenylaminopent-3-ene-2-one (175.2 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 24 hours at 120° C. After the brown oily raw product (157.3 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 94:6→0:100), the desired product was obtained in the form of a yellow oil (57.2 mg, 0.25 mmol, 25%).

Workup

  1. customAfter the brown oily raw product (157.3 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 94:6→0:100)

Sources & evidence

ORD record
ord-d9c4e2d4485c4a04a22d6162e79b26fa
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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