Pyridinium hydrochloride → 4-Chloro-2-[2-oxo-5-(trifluoromethyl)-1,2-dihydropyridin-4-yl]benzonitrile

HRID 56732

Reaction equation

HRID 56732 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][N:13]=[C:12]([O:20]C)[CH:11]=2)[CH:3]=1.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([C:16]([F:17])([F:18])[F:19])=[CH:14][NH:13][C:12](=[O:20])[CH:11]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 1176057584-Chloro-2-[2-methoxy-5-(trifluoromethyl)pyridin-4-yl]benzonitrile

Product 1

HCID 1176056274-Chloro-2-[2-oxo-5-(trifluoromethyl)-1,2-dihydropyridin-4-yl]benzonitrile

Procedure

450 mg (purity 71%, 1.02 mmol) of 4-chloro-2-[2-methoxy-5-(trifluoromethyl)pyridin-4-yl]benzonitrile and 20 eq. of pyridinium hydrochloride were reacted according to General Method 3A. After aqueous work-up, the crude product was purified by flash chromatography (silica gel 60, dichloromethane/methanol mixtures). Yield: 456 mg (purity 86%, quant.)

Workup

  1. customAfter aqueous work-up, the crude product was purified by flash chromatography (silica gel 60, dichloromethane/methanol mixtures)

Sources & evidence

ORD record
ord-d36814fdac9b4e77a07bdbd443b15151
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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