Propionitrile → HCID 53389693, compound

HRID 1020870Notes

Reaction equation

HRID 1020870 reaction equation
[C:1]1([C:7](=[O:18])/[CH:8]=[C:9](\[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19](#[N:22])[CH2:20][CH3:21]>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:20]([C:19]1[C:8]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:18])=[C:9]([CH3:10])[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:22]=1)[CH3:21]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 10955582HCID 10955582, compound

Product 1

HCID 53389693HCID 53389693, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z)-1-phenyl-3-phenylamino-but-2-ene-1-one (237.3 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. After the dark-brown bluish raw product (330.0 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→60:40→0:100), the desired product was obtained in the form of a yellow oil (126.2 mg, 0.43 mmol, 43%).

Workup

  1. customAfter the dark-brown bluish raw product (330.0 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→60:40→0:100)

Sources & evidence

ORD record
ord-abfb64095d5f4dacba88829b030f745f
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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