HCID 178418361, compound → HCID 178432492, compound

HRID 620833Notes

Reaction equation

HRID 620833 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[NH:5][C:6]=1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[H][H]>[Pd].O1CCCC1.CO>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:4]1[NH:5][C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178432493HCID 178432493, compound

Product 1

HCID 178432492HCID 178432492, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-2-(2-nitrophenyl)-5-(3-pyridyl)imidazole (4.99 g) and 10% palladium on carbon (1.0 g) in a mixture of tetrahydrofuran (150 ml) and methanol (150 ml) was hydrogenated at ambient temperature under atmospheric pressure of hydrogen gas. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was recrystallized from ethanol to give 2-(2-aminophenyl)-4-methyl-5-(3-pyridyl)imidazole (4.22 g).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-67580dfa284d4a6388b9aacb63154e7c
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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