Phosphorus oxychloride → 2-Chloro-4-(4-methoxyphenyl)pyridine

HRID 657663Notes

Reaction equation

HRID 657663 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:13]1[CH:14]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 576720264-(4-Methoxyphenyl)pyridine 1-oxide

Product 1

HCID 534408782-Chloro-4-(4-methoxyphenyl)pyridine

Procedure

A mixture of 4-(4-methoxyphenyl)pyridine 1-oxide (1.68 g) and phosphorus oxychloride (15 mL) is heated under reflux for six hours and concentrated under reduced pressure. Toluene is added and the mixture concentrated under reduced pressure. The residue is dissolved in hot toluene (20 mL) and the organic phase washed with water (twice 10 mL) a saturated aqueous sodium hydrogenocarbonate solution (10 mL), dried over magnesium sulphate and concentrated under reduced pressure to give 1.45 g of 2-chloro-4-(4-methoxyphenyl)pyridine as an orange coloured crystalline material.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for six hours
  3. concentrationconcentrated under reduced pressure
  4. additionToluene is added
  5. concentrationthe mixture concentrated under reduced pressure
  6. dissolutionThe residue is dissolved in hot toluene (20 mL)
  7. washthe organic phase washed with water (twice 10 mL) a saturated aqueous sodium hydrogenocarbonate solution (10 mL)
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e70382c90c414390892477b9fc30888c
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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