N-(5-Chloro-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide → 1-Hydroxyfluromidine

HRID 917847Notes

Reaction equation

HRID 917847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=O)[C:5]([NH:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=1.[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[N:15]([OH:17])[C:9]([C:10]([F:13])([F:12])[F:11])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 20355442N-(5-Chloro-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 30824181-Hydroxyfluromidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Chloro-3-nitro-2-(trifluoroacetamido)pyridine (2.0 grams) was hydrogenated with two moles of hydrogen in ethanol containing 0.5 gram of 5 percent palladium on carbon. The resulting reaction mixture was filtered and evaporated to separate the desired 6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo-(4,5-b)pyridine compound which, after recrystallization from benzene melted at 268°-70°C.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customto separate the desired 6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo-(4,5-b)pyridine compound which
  5. customafter recrystallization from benzene melted at 268°-70°C.

Sources & evidence

ORD record
ord-5950ce291f1e416cbe062258c97dc1d1
Source dataset
uspto-grants-1976_07
Patent number
US03968116

Reaction notes

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