Ammonium formate → 3-fluoro-4-(2-methyl-1H-imidazol-1-yl)aniline

HRID 1167470Notes

Reaction equation

HRID 1167470 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH3:13].C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[NH2:14][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 218766451-(2-fluoro-4-nitrophenyl)-2-methyl-1H-imidazole

Product 1

HCID 218766203-fluoro-4-(2-methyl-1H-imidazol-1-yl)anilineYield 100.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro4-(2-methyl-imidazol-1-yl)nitrobenzene (40 g, 0.181 M) was dissolved in a mixture of MeOH (200 ml) and tetrahydrofuran (800 ml), cooled to 0° under nitrogen, and treated with ammonium formate (57 g, 0.905 M) followed by palladium on charcoal (10%, 2 g). The mixture was stirred at ambient temperature for 18 hours, filtered through celite, celite washed with MeOH (100 ml), and filtrate evaporated to dryness. The residue was partitioned between EtOAc (800 ml) and 10% aqueous sodium bicarbonate (250 ml). The organic layer was separated, washed with brine (250 ml), dried (magnesium sulfate) and evaporated to give title compound (34.6 g).

Workup

  1. temperaturecooled to 0° under nitrogen
  2. filtrationfiltered through celite, celite
  3. washwashed with MeOH (100 ml), and filtrate
  4. customevaporated to dryness
  5. customThe residue was partitioned between EtOAc (800 ml) and 10% aqueous sodium bicarbonate (250 ml)
  6. customThe organic layer was separated
  7. washwashed with brine (250 ml)
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated

Sources & evidence

ORD record
ord-2b6f6b3e24da4c208860674f327c9b4e
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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