Thionyl Chloride → 4-(Chloromethyl)picolinonitrile hydrochloride

HRID 1384615Notes

Reaction equation

HRID 1384615 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][N:4]=1)#[N:2].S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[ClH:13].[Cl:13][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]#[N:2])[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 226250684-(Chloromethyl)picolinonitrile hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-cyano-4-hydroxymethylpyridine (0.51 g, 3.8 mmol)and thionyl chloride (0.6 ml) in toluene (20 ml) was stirred at room temperature for 1 hour. The volatiles were removed by evaporation and the residue azeotroped with toluene to give 4-chloromethyl-2-cyanopyridine hydrochloride (620 mg, 86%). 1H NMR Spectrum: (DMSOd6) 4.75(s, 2H); 7.75(dd, 1H); 8.05(s, 1H); 8.34(d, 1H)

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-f037294e524e4b3fa9cdd47c72233552
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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