Phosphorus oxychloride → 2-Chloro-3-nitro-5-(2-methylpropyl)pyridine

HRID 722054Notes

Reaction equation

HRID 722054 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:17])=O.[Na].C(=O)([O-])O>>[Cl:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 50987224Sodium hydrogen-carbonateHCID 1784413372-Hydroxy-3-nitro-5-(2-methylpropyl)pyridine2×

Product 1

HCID 218827262-Chloro-3-nitro-5-(2-methylpropyl)pyridine

Conditions

Temperature
120 °C

Procedure

A mixture of 1.7 g of 2-hydroxy-3-nitro-5-(2-methylpropyl)pyridine (starting material D4) and 15 ml of phosphorous oxychloride is heated under reflux to 120° C. for two hours. After cooling the mixture is carefully added to ice/water, then neutralized with sodium-hydrogencarbonate and extracted three times with ethylacetate. The combined organic phases are evaporated to dryness and the residue is chromatographed on a silica gel column (ethylacetate/petroleum ether 1:15). Concentration of the chromatographically pure fractions gives 1.17 g of the title compound as an orange oil.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling the mixture
  3. extractionextracted three times with ethylacetate
  4. customThe combined organic phases are evaporated to dryness
  5. customthe residue is chromatographed on a silica gel column (ethylacetate/petroleum ether 1:15)

Sources & evidence

ORD record
ord-bf5a6deaea9f441fb5f3f6c70fa43b82
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

Loading…