Phosphorus oxychloride → 6-Chloro-4-(o-tolyl)nicotinonitrile

HRID 1182373Notes

Reaction equation

HRID 1182373 reaction equation
O[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:19])=O>ClCCl>[Cl:19][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424179HCID 178424179, compound

Product 1

HCID 113681836-Chloro-4-(o-tolyl)nicotinonitrileYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.5 g (11.89 mmol) 6-hydroxy-4-o-tolyl-nicotinonitrile, 3.64 g (23.78 mmol) phosphorus oxychloride in 10.0 ml dichloromethane was heated at 50° C. for 80 minutes. The mixture was cooled down to 20-25° C., poured on water by keeping the internal temperature between 20-30° C. and extracted by adding additional 80.0 ml dichloromethane. Evaporation of the organic phase in vacuo gave 2.9 g of crude product of 6-chloro-4-o-tolyl-nicotinonitrile which was purified by chromatography over silica gel (ethylacetate:hexane=4:1) to afford 2.4 g of, m.p. 112.4° C.

Workup

  1. temperatureThe mixture was cooled down to 20-25° C.
  2. additionpoured on water
  3. custombetween 20-30° C.
  4. extractionextracted
  5. additionby adding additional 80.0 ml dichloromethane
  6. customEvaporation of the organic phase in vacuo

Sources & evidence

ORD record
ord-caf503acd14a434887f37615c1de9f6f
Source dataset
uspto-grants-2007_10
Patent number
US07288658B2

Reaction notes

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