Propionitrile → HCID 53389675, compound

HRID 1020869Notes

Reaction equation

HRID 1020869 reaction equation
[CH2:1]([O:8][C:9](=[O:21])/[CH:10]=[C:11](\[NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)/[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](#[N:25])[CH2:23][CH3:24]>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([O:8][C:9]([C:10]1[C:22]([CH2:23][CH3:24])=[N:25][N:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:11]=1[CH3:12])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 67449278HCID 67449278, compound

Product 1

HCID 53389675HCID 53389675, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-3-(4-fluorophenylamino)-but-2-enoic acid benzylester (285.3 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 purification by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→70:30→0:100), the product was obtained in the form of a yellow oil (283.0 mg, 0.84 mmol, 84%).

Workup

  1. customAfter purification by means of column chromatography (silica gel (50 g), pentane/EtOAc 98:2→70:30→0:100)

Sources & evidence

ORD record
ord-a1fdefb633d649c4a04020c1531e290d
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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