Hexane → 2-Chloro-5-(chloromethyl)pyridine

HRID 1457870Notes

Reaction equation

HRID 1457870 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][Cl:10])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].CCCCCC>O>[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][Cl:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 224503272-Chloro-5-chloromethylpyridine hydrochloride

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridineYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 50 ml of water was suspended 15.0 g (0.076 mole) of 6-chloro-3-pyridylmethyl chloride hydrochloride and the suspension was adjusted to pH about 8 with a saturated aqueous solution of sodium hydrogen carbonate. The resulting mixture was extracted with ether (100 ml×3) and dried over MgSO4. The ether was then distilled off under reduced pressure to give a crystalline residue. After addition of hexane, the crystals were recovered by filtration, washed with hexane and dried to give 11.0 g of 6-chloro-3-pyridylmethyl chloride as white prisms.

Workup

  1. extractionThe resulting mixture was extracted with ether (100 ml×3)
  2. dry with materialdried over MgSO4
  3. distillationThe ether was then distilled off under reduced pressure
  4. customto give a crystalline residue
  5. filtrationthe crystals were recovered by filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-b877cafb34a74f5184d4bfa675e755f3
Source dataset
uspto-grants-1998_12
Patent number
US05849768

Reaction notes

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