Phosphorus oxychloride → 2-(tert-Butyl)-4-chloropyridine

HRID 1430112Notes

Reaction equation

HRID 1430112 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([C:10]1[CH2:15][C:14](=O)[CH:13]=[CH:12][N:11]=1)([CH3:9])([CH3:8])[CH3:7]>C(Cl)(Cl)Cl>[Cl:3][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])[CH:15]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 687364792-Tert.butylpyridin-4-one

Product 1

HCID 580879812-(tert-Butyl)-4-chloropyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Phosphorous oxychloride (21.8 ml) and 2-tert.butylpyridin-4-one (2.36 g) is heated at reflux in chloroform (15 ml) for 24 hours and then stood at room temperature for 48 hours before pouring onto ice (100 g). Extraction with CH2Cl2 (3 times 250 ml) is followed by drying of the combined organic layers over magnesium sulphate. Evaporation of the organic layers gives the title compound.

Workup

  1. additionbefore pouring onto ice (100 g)
  2. extractionExtraction with CH2Cl2 (3 times 250 ml)
  3. dry with materialby drying of the combined organic layers over magnesium sulphate
  4. customEvaporation of the organic layers

Sources & evidence

ORD record
ord-af6dbfe80d704378a8679a0d2b69f85c
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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