Water → 2,3-Dimethyl-4-nitropyridine

HRID 1988853Notes

Reaction equation

HRID 1988853 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][N+:3]=1[O-].P(Cl)(Cl)Cl.O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Product 1

HCID 112173482,3-Dimethyl-4-nitropyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

2,3-Dimethyl-4-nitropyridin-N-oxide (75.6 g, 0.45 mol) prepared in Step 1 was dissolved in 300 ml of methylene chloride. A solution of phosphorus trichloride (44 ml) in methylene chloride (60 ml) was slowly added to the solution for 30 minutes at −15° C.˜−20° C. The reaction mixture was stirred for 15 minutes at the same temperature and further stirred for 15 minutes at room temperature. The reaction mixture was cooled to −78° C. 50 ml of water was added to the reaction mixture, which was neutralized with a sodium hydroxide solution and then extracted with methylene chloride. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound as a pale yellow solid (65 g, 95%).

Workup

  1. stirringfurther stirred for 15 minutes at room temperature
  2. extractionextracted with methylene chloride
  3. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2920229c62f4df39ff28c32324b4d0d
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

Loading…