Phosphorus oxychloride → 6-Chloro-2,4-dimethyl-5-nitronicotinonitrile

HRID 724059Notes

Reaction equation

HRID 724059 reaction equation
O[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[C:5]([C:6]#[N:7])=[C:4]([CH3:14])[N:3]=1.P(Cl)(Cl)([Cl:17])=O>O>[Cl:17][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([CH3:13])[C:5]([C:6]#[N:7])=[C:4]([CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178433489HCID 178433489, compound

Product 1

HCID 218761896-Chloro-2,4-dimethyl-5-nitronicotinonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-hydroxy-2,4-dimethyl-5-nitronicotinonitrile (step 2, 3.2 g, 16.6 mmol) and phosphorus oxychloride (20 mL) was stirred at 100° C. for 16 h. After cooling, the mixture was poured in water (100 mL). The resulting mixture was extracted with dichloromethane (3×100 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and concentrated to afford 2.3 g (66%) of the title compound as brown solids: 1H-NMR (DMSO-d6) δ 2.82 (3H, s), 2.52 (3H, s).

Workup

  1. temperatureAfter cooling
  2. extractionThe resulting mixture was extracted with dichloromethane (3×100 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ab8d2eb94746f0a37b0ec7a9d8fef8
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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