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

HRID 1582336Notes

Reaction equation

HRID 1582336 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-Fluoro-4-(2-methylimidazol-1-yl)nitrobenzene (40 g, 0.181 M) was dissolved in a mixture of methanol (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 methanol (100 ml), and filtrate evaporated to dryness. The residue was partitioned between ethyl acetate (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). NMR (DMSO-d6) δ: 2.08 (s, 3H); 5.68 (s, 2H); 6.45 (overlapping m, 2H); 6.84 (d, 1H); 7.03 (overlapping m, 2H). MS (ESP): 192 (MH+) for C10H10FN3

Workup

  1. temperaturecooled to 0° under nitrogen
  2. filtrationfiltered through celite, celite
  3. washwashed with methanol (100 ml), and filtrate
  4. customevaporated to dryness
  5. customThe residue was partitioned between ethyl acetate (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-bf6eb09c0e254b9ea54987f2ad26e2c7
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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