Ammonia → 2-Chloro-5-(trifluoromethyl)nicotinamide

HRID 2089245Notes

Reaction equation

HRID 2089245 reaction equation
[NH3:1].[Cl:2][C:3]1[N:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:4]=1[C:5](Cl)=[O:6]>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[N:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:4]=1[C:5]([NH2:1])=[O:6]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 378634602-Chloro-5-(trifluoromethyl)pyridine-3-carbonyl chloride

Product 1

HCID 734250142-Chloro-5-(trifluoromethyl)nicotinamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

An ice-cold solution of ammonia in water was treated with a solution of 2-chloro-5-(trifluoromethyl)nicotinoyl chloride (as prepared in the previous step, 1.18 g, 4.8 mmol) in dioxane. After stirring at ice bath temperature for 1 hour, the resulting precipitate was dissolved in ethyl acetate and the organic extract dried over anhydrous sodium sulfate. Concentration in vacuo followed by drying on the high vacuum afforded the product as a white solid.

Workup

  1. extractionthe organic extract
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationConcentration in vacuo
  4. customby drying on the high vacuum

Sources & evidence

ORD record
ord-4dd0051a5990483b917d9d99b0dde0f6
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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