Hydrochloric Acid → 6-Amino-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-1-ol

HRID 371663Notes

Reaction equation

HRID 371663 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]([OH:13])[C:11]([C:14]([F:17])([F:16])[F:15])=[N:10][C:7]2=[N:8][CH:9]=1)([O-])=O.C(O)C.Cl.[H][H]>[Pd].O>[NH2:1][C:4]1[CH:5]=[C:6]2[N:12]([OH:13])[C:11]([C:14]([F:15])([F:17])[F:16])=[N:10][C:7]2=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 203554946-Nitro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 203554676-Amino-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridin-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

6-Nitro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine (4.9 grams) was mixed with 100 milliliters of ethanol and 3 milliliters of concentrated hydrochloric acid, and 1 gram of 5 percent palladium on carbon was added to the mixture. The mixture was hydrogenated to a 3 mole-equivalent uptake of hydrogen. The reaction mixture was then filtered and evaporated, yielding a gummy solid residue which was taken up in 150 milliliters of water and used directly in the reaction reported in the following example.

Workup

  1. additionwas added to the mixture
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated
  4. customyielding a gummy solid residue which

Sources & evidence

ORD record
ord-9ee81935c37245bd9899f682e25f1938
Source dataset
uspto-grants-1978_05
Patent number
US04087432

Reaction notes

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