Dichloromethane → 2,4-Dichloro-5,6-dimethyl-3-nitropyridine

HRID 639694Notes

Reaction equation

HRID 639694 reaction equation
[CH3:1][C:2]1C(O)=[C:4]([N+:10]([O-:12])=[O:11])[C:5](O)=[N:6][C:7]=1[CH3:8].P(Cl)(Cl)([Cl:16])=O.[CH2:19]([Cl:21])Cl>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[Cl:16][C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[C:19]([Cl:21])[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178433492HCID 178433492, compound

Product 1

HCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineYield 75%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

5,6-Dimethyl-3-nitro-pyridin-2,4-diol (3.9 g, 21 mmol) was dissolved in acetonitrile (150 mL) and firstly tetraethylammonium chloride (7.1 g, 42 mmol) and then phosphorus oxychloride (19.9 mL, 210 mmol) were added and the whole heated at 70C for 16 h. The reaction mixture was poured into crushed ice and extracted with DCM (2×30 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to afford a brown solid. This solid was taken up in 2 mL DCM and filtered through a short plug of silica gel eluting with 2:1 pentane:EtOAc. The filtrate was then evaporated to afford the title compound as a light brown solid (3.5 g, 75%).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. extractionextracted with DCM (2×30 mL)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a brown solid
  8. filtrationfiltered through a short plug of silica gel eluting with 2:1 pentane
  9. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-a306f18392ac4a54914a33ad6308bce5
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

Loading…