Potassium Hydroxide → 4-Trifluoromethylnicotinamide

HRID 1744276Notes

Reaction equation

HRID 1744276 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3](=O)[CH:4]=[CH:5][NH:6][CH:7]=[CH:8][C:9]#[N:10].[OH-].[K+].CCCCCC.CC(C)=[O:24]>CO>[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([NH2:10])=[O:24])=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21880519Acetone hexaneHCID 731022503-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

Product 1

HCID 27826434-TrifluoromethylnicotinamideYield 52.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 1.90 g, 10 mmol) was dissolved in methanol (15 ml), and potassium hydroxide (990 mg, 15 mmol) was added. The mixture was heated under reflux for 6 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/acetone=1/1) to obtain 1.03 g (yield 52.6%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (a eluting solvent

Sources & evidence

ORD record
ord-79ce498eb463465383ce9bf3be41c0a6
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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