N,N-Dimethylaniline → 2,4-Dichloro-3,6-dimethylpyridine

HRID 968026Notes

Reaction equation

HRID 968026 reaction equation
O[C:2]1[C:7](C)=[C:6](O)[CH:5]=[C:4]([CH3:10])[N:3]=1.O=P(Cl)(Cl)[Cl:13].CN(C)C1C=CC=CC=1.[CH:25]([Cl:28])(Cl)Cl>>[Cl:13][C:2]1[C:7]([CH3:6])=[C:25]([Cl:28])[CH:5]=[C:4]([CH3:10])[N:3]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 178429043HCID 178429043, compound

Product 1

HCID 110843982,4-Dichloro-3,6-dimethylpyridine

Procedure

A mixture of 2,4-dihydroxy-3,6-dimethylpyridine (2.86 g, 20.58 mmol), POCl3 (15 ml) and N,N-dimethylaniline (3.6 ml, 22.64 mmol) was heated at reflux for 3 hours. The mixture was cooled, poured into ice water and extracted with diethyl ether. The organic layer was dried and concentrated to give 3.02 g of the crude material. After silica gel column chromatography using chloroform as eluent, 1.3102 g of the title compound was obtained as a yellow oil. 1H NMR (CDCl3) δ 7.07 (s, 1H), 2.43 (s, 3H), 2.39 (s, 3H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give 3.02 g of the crude material

Sources & evidence

ORD record
ord-2e5d1df4f1034a0b9e9e64ad6d1d28e7
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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