Phosphorus pentachloride → 2-Chloro-5,6-dimethyl-3-nitropyridine

HRID 489260Notes

Reaction equation

HRID 489260 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5](=O)[NH:6][C:7]=1[CH3:8].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>>[Cl:14][C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 2646205,6-Dimethyl-3-nitro-1,2-dihydropyridin-2-one

Product 1

HCID 100811492-Chloro-5,6-dimethyl-3-nitropyridineYield 90.2%

Conditions

Temperature
140 °C

Procedure

5,6-Dimethyl-3-nitro-2-pyridone (1-013-04)(841 mg) and phosphorus pentachloride (1.25 g) was heated with stirring in an oil bath at 140° C. under nitrogen atmosphere. After 35 min, the reaction mixture was cooled under ice-cooling, poured into ice-water, extracted with twice with chloroform, and washed once with water and a saturated aqueous solution of sodium bicarbonate. To the extract was added a decolorzing charcoal, and the extract was dried over magnesium sulfate, and evaporated under reduced pressure to give 2-chloro-5,6-dimethyl-3-nitropyridine (1-013-05) (842 mg, 90.2%) as a crystalline residue.

Workup

  1. temperaturethe reaction mixture was cooled under ice-
  2. temperaturecooling
  3. extractionextracted with twice with chloroform
  4. washwashed once with water
  5. additionTo the extract was added a decolorzing charcoal
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-88d5798d2ff94e938deadb035fb0596f
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

Loading…