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

HRID 1734497Notes

Reaction equation

HRID 1734497 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-38e765cc58ff48c9bd3a04b4719db8e0
Source dataset
uspto-grants-1996_07
Patent number
US05534485

Reaction notes

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