2-(N-methylcarbamoyl)-5-tert-butyl-3-nitropyrrole → 2-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrrole

HRID 1698917Notes

Reaction equation

HRID 1698917 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[N+:10]([O-])=O)=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 1

HCID 183223572-(N-methylcarbamoyl)-5-tert-butyl-3-nitropyrrole

Product 1

HCID 183223852-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrroleYield 781%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(N-methylcarbamoyl)-5-tert-butyl-3-nitropyrrole (1.0 g, 0.4 mmol) in EtOAc (50 mL) under an Ar atmosphere was added 10% Pd/C (50 mg). The mixture was evacuated then placed under a static H2 atmosphere (1 atm.) for 24 h. The resulting slurry was filtered through a pad of Celite® with the aid of EtOAc, and the filtrate was concentrated under reduced pressure to afford 2-(N-methylcarbamoyl)-3-amino-5-tert-butylpyrrole (0.61 g, 70%): 1H-NMR (DMSO-d6) δ1.16 (s, 9H), 2.66 (d, J=4.41 Hz, 3H), 4.89 (br s, 2H), 5.27 (d, 2.58 Hz, 1H), 7.14-7.16 (m, 1H), 9.52 (br s, 1H).

Workup

  1. customThe mixture was evacuated
  2. customfor 24 h
  3. filtrationThe resulting slurry was filtered through a pad of Celite® with the aid of EtOAc
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd8d8d96f0094c83b3f658e5ae260fed
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

Loading…