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

HRID 2074069Notes

Reaction equation

HRID 2074069 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. In a hydrogenation apparatus, the reaction mixture is hydrogenated with hydrogen at room temperature. The catalyst is filtered off and the filtrate is concentrated in vacuo. The concentration residue is directly used further for the next reaction.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe concentration residue is directly used further for the next reaction

Sources & evidence

ORD record
ord-c4b9b8d57d234046a9bf3b6c3026b5f2
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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