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

HRID 2074066Notes

Reaction equation

HRID 2074066 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 under reflux for about 6 h. A total of 8 g of 10% palladium-on-carbon and 18 g of ammonium formate are thereby added in small portions. After cooling, the catalyst is filtered off and the filtrate is concentrated in vacuo. The product that crystallizes out during this operation is triturated with 80 ml of ice-water and collected by suction filtration.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for about 6 h
  3. temperatureAfter cooling
  4. filtrationthe catalyst is filtered off
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe product that crystallizes out during this operation
  7. customis triturated with 80 ml of ice-water
  8. filtrationcollected by suction filtration

Sources & evidence

ORD record
ord-e91d301b82cd44dea71810d53277e9a0
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

Loading…