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

HRID 2277412Notes

Reaction equation

HRID 2277412 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH:8]=[C:9]([N+:11]([O-])=O)[N:10]=1)=[O:5])[CH3:2].[H][H]>C1COCC1.[Ni]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:14][CH:15]2[CH2:16][CH2:17]2)[CH:8]=[C:9]([NH2:11])[N:10]=1)=[O:5])[CH3:2]

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 1-(cyclopropylmethyl)-4-nitro-1H-imidazole-2-carboxylic acid ethyl ester is dissolved in 50 ml of THF and mixed with a spatula tip full of Raney nickel. The reaction mixture is hydrogenated with hydrogen in a hydrogenating apparatus at room temperature. The catalyst is filtered off, and the filtrate is concentrated by evaporation in a vacuum. The evaporation residue is reused immediately for the next reaction.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by evaporation in a vacuum
  3. customThe evaporation residue is reused immediately for the next reaction

Sources & evidence

ORD record
ord-8c68ebd83b1048bd9b8cb5197a5b0f74
Source dataset
uspto-grants-2015_09
Patent number
US09133165B2

Reaction notes

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