3-Nitro-5-(trifluoromethyl)pyridin-2-amine → HCID 20355508, compound

HRID 1658355Notes

Reaction equation

HRID 1658355 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=O)[C:6]([NH2:9])=[N:7][CH:8]=1>FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>[OH:12][N:10]1[C:5]2[C:6](=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:14])[F:13])[CH:4]=2)[N:9]=[C:3]1[C:2]([F:14])([F:13])[F:1]

Participants

4

Reactant 1

HCID 106083913-Nitro-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 20355508HCID 20355508, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

5-(Trifluoromethyl)-3-nitro-2-aminopyridine (10.0 grams) in trifluoroacetic anhydride (10 ml.) and pyridine (20 ml.) were heated in a steam bath for two hours. Solvents were then evaporated on a rotary evaporator at 100°C. for one hour, and the residue was taken up in ethyl acetate and hydrogenated over 2.0 g. of 5 percent palladium on carbon. The reaction mixture was then filtered, evaporated, and taken up in ethanol; subsequently, the mixture was washed with 10 percent hydrochloric acid, dried over magnesium sulfate, and evaporated. The resulting 1-hydroxy-2,6-bis(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product was recrystallized from acetone, m.p., 239°-40°C.

Workup

  1. customSolvents were then evaporated on a rotary evaporator at 100°C. for one hour
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated
  4. washsubsequently, the mixture was washed with 10 percent hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe resulting 1-hydroxy-2,6-bis(trifluoromethyl)-1H-imidazo(4,5-b)pyridine product was recrystallized from acetone, m.p., 239°-40°C.

Sources & evidence

ORD record
ord-05f8a6f1d4b64faea7276faf8d7dddd7
Source dataset
uspto-grants-1976_06
Patent number
US03963734

Reaction notes

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