Ethyl 1-methyl-4-nitroimidazole-2-carboxylate → ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

HRID 2074072Notes

Reaction equation

HRID 2074072 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[N:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)C.[Pd]>[NH2:7][C:5]1[N:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:2]([CH3:1])[CH:6]=1

Participants

4

Reactant 1

HCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

Product 1

HCID 7006687ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.50 g (2.5 mmol) of ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate are dissolved in 7.5 ml of ethanol, 0.13 g (0.13 mmol) of palladium-on-carbon (10%) are added and the mixture is hydrogenated at 3 bar for 12 h. The reaction solution is then filtered through kieselguhr and the filtrate is concentrated. The residue is dried in vacuo and reacted further without further purification.

Workup

  1. filtrationThe reaction solution is then filtered through kieselguhr
  2. concentrationthe filtrate is concentrated
  3. customThe residue is dried in vacuo
  4. customreacted further without further purification

Sources & evidence

ORD record
ord-aba1432f81f14837a728df53eb54db87
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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