Sodium Cyanide → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 47881Notes

Reaction equation

HRID 47881 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[C:6](F)=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>O.C(#N)CC.CN(C)C1C=CN=CC=1>[Cl:4][C:5]1[C:6]([C:1]#[N:2])=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileYield 83%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 7854PropionitrileSolvent

Conditions

Temperature
20 °C

Procedure

A reactor was charged with a solution of sodium cyanide (73.5 g) in water (150 ml), propionitrile (500 ml), 4-dimethylaminopyridine (16 g), and 3-chloro-2-fluoro-5-trifluoromethylpyridine (149.3 g) added over 30 minutes. After stirring for 5 hours at 20° C., the upper organic phase was separated off and washed with water. The lower aqueous layer was extracted with propionitrile, the two organic layers combined and solvent distilled off under vacuum at 45° C. to give an 83% yield of 3-chloro-2-cyano-5-trifluoromethylpyridine.

Workup

  1. additionadded over 30 minutes
  2. customthe upper organic phase was separated off
  3. washwashed with water
  4. extractionThe lower aqueous layer was extracted with propionitrile
  5. distillationsolvent distilled off under vacuum at 45° C.

Sources & evidence

ORD record
ord-25f66ee5310c437fb8f594e64e59f8fe
Source dataset
uspto-grants-2004_03
Patent number
US06699993B1

Reaction notes

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