Phosphorus oxychloride → 2-Chloro-6-methyl-4-(trifluoromethyl)pyridine-3-carbonitrile

HRID 1501121Notes

Reaction equation

HRID 1501121 reaction equation
O[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178426048HCID 178426048, compound

Product 1

HCID 125364092-Chloro-6-methyl-4-(trifluoromethyl)pyridine-3-carbonitrileYield 90%

Procedure

To 2-hydroxy-6-methyl-4-(trifluoromethyl)nicotinonitrile (1 g, 5 mmol) was added phosphoryl trichloride (15 mL). Then the mixture was heated to reflux and maintained at the same temperature with stirring for 2 hours. The resultant mixture was concentrated to give a residue and the residue was purified by chromatography (petroleum ether/ethyl acetate=1:1) to give 2-chloro-6-methyl-4-(trifluoromethyl)nicotinonitrile (1 g, 90%). 1H NMR (300 MHz, CD3OD): δ 7.81 (s, 1H), 2.70 (s, 3H).

Workup

  1. temperatureThen the mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained at the same temperature
  4. concentrationThe resultant mixture was concentrated
  5. customto give a residue
  6. customthe residue was purified by chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7262f863070048659e6758d2c3994c00
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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