methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate → methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

HRID 1698912

Reaction equation

HRID 1698912 reaction equation
[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:14][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[NH:9][C:8]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 18322358methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 18322367methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 5-tert-butyl-3-nitropyrrole-2-carboxylate (0.014 g, 0.062 mmol) and 10% Pd/C (3 mg) in dry MeOH (1 mL) was successively evacuated and purged with H2 three times, then shaken under an atmosphere of H2 (35 psi) for 1 h, diluted with CH2Cl2 and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give methyl 3-amino-5-tert-butylpyrrole-2-carboxylate as a bright yellow oil (0.012 g, 100%). 1H NMR (CDCl3) δ1.26 (s, 9H), 3.82 (s, 3H), 5.52 (d, J=2.8 Hz, 1H), 7.89 (br s, 2H). This material was used in the next step without further purification.

Workup

  1. customwas successively evacuated
  2. custompurged with H2 three times
  3. additiondiluted with CH2Cl2
  4. filtrationfiltered through a pad of Celite®
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ed61ba318064bc58cbbdf6a8ad0925c
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Linked notes

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