Ammonium formate → ethyl 1H-imidazole-2-carboxylate

HRID 499901Notes

Reaction equation

HRID 499901 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 39869052ethyl 1-benzyl-1H-imidazole-2-carboxylate

Product 1

HCID 549404ethyl 1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

34.7 g (150.9 mmol) of ethyl 1-benzyl-1H-imidazole-2-carboxylate are dissolved in 1005 ml of ethanol, and 34 g of ammonium formate are added. The reaction mixture is heated to reflux for about 6 h. Then a total of 8 g of 10% palladium on activated carbon and 18 g of ammonium formate is added in small portions. After cooling, the catalyst is filtered off and the filtrate is concentrated in vacuo. The product which crystallizes out is stirred in 80 ml of ice-water and filtered off with suction.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for about 6 h
  3. temperatureAfter cooling
  4. filtrationthe catalyst is filtered off
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe product which crystallizes out
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-9793e35a25424d73801663ea7195de6c
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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