Phosphorus oxychloride → 2-(4-Methylphenyl)-6-chloromethylpyridine

HRID 1077840Notes

Reaction equation

HRID 1077840 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N+:9]=2[O-])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:18])=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Cl:18])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 194303302-(4-methylphenyl)-6-methylpyridine-N-oxide

Product 1

HCID 194303092-(4-Methylphenyl)-6-chloromethylpyridine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(4-methylphenyl)-6-methylpyridine-N-oxide (2.8 g) in 10 ml of chloroform was added simultaneously phosphorus oxychloride (1.48 ml) in 10 ml of chloroform and triethylamine (2.22 ml) in 10 ml of chloroform, over a period of 15 minutes. An exothermic reaction took place initially, and then the mixture was refluxed for a further 30 minutes. The mixture was then cooled, washed with ice-water, the solvent evaporated under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 33% methylene chloride in heptane, to yield 1 g of 2-(4-methylphenyl)-6-chloromethylpyridine, m.p. 94° C.

Workup

  1. customAn exothermic reaction
  2. temperaturethe mixture was refluxed for a further 30 minutes
  3. temperatureThe mixture was then cooled
  4. washwashed with ice-water
  5. customthe solvent evaporated under reduced pressure
  6. customthe residue flash-chromatographed on silica gel
  7. washeluting with 33% methylene chloride in heptane

Sources & evidence

ORD record
ord-6900546f3d5e4ad7baebb7cb46b7607f
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Reaction notes

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