Ethyl 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylate → Ethyl 4-amino-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylate

HRID 499904Notes

Reaction equation

HRID 499904 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([N+:10]([O-])=O)[N:7]=[C:6]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3][CH2:2]1.[H][H]>C1COCC1.[Ni]>[NH2:10][C:8]1[N:7]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH:9]=1

Participants

5

Reactant 2

HCID 59421751Ethyl 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59421792Ethyl 4-amino-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.89 g (16.26 mmol) of ethyl 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylate are dissolved in 50 ml of THF, and a spatula tip of Raney nickel is added. The reaction mixture is hydrogenated with hydrogen in the hydrogenation apparatus at room temperature. The catalyst is filtered off and the filtrate is evaporated in vacuo. The residue from evaporation is further used directly for the next reaction.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. customThe residue from evaporation
  4. customis further used directly for the next reaction

Sources & evidence

ORD record
ord-67873080b3c841fbad7436472a08d583
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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