Pyridine → 5-(Chloromethyl)pyridine-2-carbonitrile

HRID 1193964Notes

Reaction equation

HRID 1193964 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][N:4]=1)#[N:2].N1C=CC=CC=1.C1(C)C=CC(S([Cl:26])(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Cl:26])=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 122519662-Cyano-5-hydroxymethylpyridine

Product 1

HCID 144051235-(Chloromethyl)pyridine-2-carbonitrileYield 50.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-Cyano-5-hydroxymethylpyridine (13.4 g) and pyridine (8.7 g) were dissolved in toluene (150 ml), and a solution of p-toluenesufonyl chloride (19.1 g) in toluene (50 ml) was added dropwise at room temperature to the solution. After the addition, the mixture was gradually heated, and stirred at 70° to 80° C. for 4 hours. The reaction mixture was cooled to room temperature, and washed with water. The organic layer was dried. Toluene was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2-cyano-5-pyridylmethyl chloride (7.7 g) as colorless crystals.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was gradually heated
  3. washwashed with water
  4. customThe organic layer was dried
  5. distillationToluene was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b033bdf95c3497986859f01efe950f0
Source dataset
uspto-grants-1989_03
Patent number
US04812454

Reaction notes

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