Triethylamine → 6-(Chloromethyl)pyridine-3-carbonitrile

HRID 1086876Notes

Reaction equation

HRID 1086876 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH3:15])=[N+:12]([O-])[CH:13]=1)#[N:7].C(N(CC)CC)C>ClCCl>[Cl:3][CH2:15][C:11]1[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 198186716-Methylpyridine-3-carbonitrile 1-oxide

Product 1

HCID 149805356-(Chloromethyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosphoryl chloride (6.5 g) in dichloromethane (20 ml) was added to a mixture of the above pyridine-1-oxide (4.4 g) and triethylamine (4.3 g) in dichloromethane (60 ml). After the addition was completed the reaction mixture was gently refluxed for 15 mins, cooled and washed with water (30 ml). The organic layer was separated, dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by flash column chromatography on silica (K60) using ethyl acetate: toluene (1:9 by volume) as eluting solvent, to give 6-chloromethylnicotinonitrile.

Workup

  1. additionAfter the addition
  2. temperaturewas gently refluxed for 15 mins
  3. temperaturecooled
  4. washwashed with water (30 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography on silica (K60)
  9. washas eluting solvent

Sources & evidence

ORD record
ord-c71b548f7e9e4c00ad288d32cec5daee
Source dataset
uspto-grants-1991_07
Patent number
US05032607

Reaction notes

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