Ammonia → 2,6-Bis(trifluoromethyl)pyridin-4-amine

HRID 1065752Notes

Reaction equation

HRID 1065752 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[NH3:16]>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[NH2:16][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 129452364-Chloro-2,6-bis(trifluoromethyl)pyridine

Product 1

HCID 6154562,6-Bis(trifluoromethyl)pyridin-4-amine

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-2,6-bis(trifluoromethyl)pyridine (50 g, 0.20 mole) in concentrated ammonia (250 ml, density 0.88) and ethanol (250 ml) containing copper sulphate (ca. 0.5 g) was stirred and heated in a pressure vessel at 100°-120° C. for 5 hours. The mixture was cooled, extracted with methylene chloride and dried over MgSO4. The solvent was removed under reduced pressure leaving the title compound as a cream solid. The product was recovered in a yield of 26 g, (56% of theoretical), m.p. 147°-149° C.

Workup

  1. temperatureheated in a pressure vessel at 100°-120° C. for 5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-30ef6e9fe9f94f8791f3bdd095f6bdef
Source dataset
uspto-grants-1982_05
Patent number
US04331669

Reaction notes

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