Benzoyl Peroxide → 3-(Chloromethyl)pyridine-2-carbonitrile

HRID 366779Notes

Reaction equation

[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:28]C1C=CC=CC=1>>[C:1]([C:3]1[C:8]([CH2:9][Cl:28])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

Reactant 3

HCID 7187Benzoyl Peroxide

HCID 7964Chlorobenzene

HCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 227477993-(Chloromethyl)pyridine-2-carbonitrile

Procedure

The 2-cyano-3-chloromethylpyridine was prepared by chlorination of 2-cyano-3-methylpyridine in chlorobenzene with benzoylperoxide by gradual addition of SO2Cl2 at 80° C. 2-Cyano-3-chloromethylpyridine was obtained in 60-65% conversion. The main impurities are 2-cyano-3-dichloromethylpyridine and unreacted 2-cyano-3-methylpyridine, which do not cause problems in the process of this Preparation.

Sources & evidence

ORD record: ord-29b9afbe84e3483794e90e9a2064e210
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130229

Reaction notes

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