Thionyl Chloride → 4-(Chloromethyl)picolinonitrile hydrochloride

HRID 1737564Notes

Reaction equation

HRID 1737564 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

1H NMR Spectrum: (DMSOd6) 4.65(s, 2H); 5.70(t, 1H); 7.70(d, 1H); 7.95(s, 1H); 8.75(d, 1H) A mixture of 2-cyano-4-hydroxymethylpyridine (0.51 g, 3.8mmol) 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%).

Workup

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

Sources & evidence

ORD record
ord-c01bc805f6ed4b43931c2070d0a1571f
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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