Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate → Ethyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate

HRID 1655878Notes

Reaction equation

HRID 1655878 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[CH:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)C.[Pt]>[NH2:7][C:5]1[CH: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 10442704Ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 11182847Ethyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 1-methyl-4-nitro-2-pyrrolecarboxylate (16.0 g, 0.081 mol) (M. J. Weiss, J. S. Webb and J. M. Smith, J. Amer. Chem. Soc., 79, 1266 (1957)) is dissolved in (200 mL) ethanol and (1.60 g) of 10% platinum on carbon is then added. The mixture is shaken for 16 hours in a PARR hydrogenator. The catalyst is removed by filtration through a pad of celite and the filtrate is concentrated in vacuo to a yellow oil. The oil is carried on directly without purification.

Workup

  1. customThe catalyst is removed by filtration through a pad of celite
  2. concentrationthe filtrate is concentrated in vacuo to a yellow oil
  3. customdirectly without purification

Sources & evidence

ORD record
ord-fb0604d3b8b546e9b450e81b12fb92cb
Source dataset
uspto-grants-1993_10
Patent number
US05252538

Reaction notes

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