Ammonium formate → ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate

HRID 2366879Notes

Reaction equation

HRID 2366879 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[CH:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18726773ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate

Product 1

HCID 18726772ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium(0) (10% w/w on carbon, 50% wet, 1.25 g, 47.8 mmol) was added to a solution of ethyl 1-(4-nitrophenyl)-1H-imidazole-4-carboxylate (for a preparation see Intermediate 86) (12.5 g, 47.8 mmol) and ammonium formate (7.54 g, 120 mmol) in ethanol (250 mL). The reaction mixture was refluxed for 4 h then cooled to room temperature and filtered through celite. The solvent was removed in vacuo to give ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate (9.41 g, 40.7 mmol, 85%) as a colourless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationfiltered through celite
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b7f680a8a8de4859b2e6212ea2acdd8d
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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