Ammonium Hydroxide → 5-(Trifluoromethyl)pyridine-2-carbonitrile

HRID 586062Notes

Reaction equation

HRID 586062 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=1.[NH4+].[OH-]>CS(C)=O>[F:12][C:11]([F:14])([F:13])[C:8]1[CH:9]=[CH:10][C:5]([C:2]#[N:3])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 15353725-(Trifluoromethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

Copper (I) cyanide (14.1 g) and 2-bromo-5-trifluoromethylpyridine (3.00 g, 13.3 mmol) in dry DMSO (70 mL) were combined and heated at 180° C. for 2 hours, cooled, and poured into NH4OH (3M). The mixture was then extracted with ethyl acetate (3×500 mL), washed with water (1×200 mL), dried (MgSO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound. 1H NMR (DMSO, 300 MHz) δ 8.22 (m, 1H), 8.42 (m, 1H), 9.01 (s, 1H).

Workup

  1. temperaturecooled
  2. extractionThe mixture was then extracted with ethyl acetate (3×500 mL)
  3. washwashed with water (1×200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0d0e9a7aa5c432b974195bf7b4d3afb
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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