Ethyl Acetate → 5-Tert-butyl-2-(2,5-dimethylpyrrolyl)aniline

HRID 78305Notes

Reaction equation

HRID 78305 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](N2C(C)=CC=C2C)=[C:7]([N+:18]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCO[C:24]([CH3:26])=O>[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[C:7]([CH3:8])[NH:18][C:24]=2[CH3:26])=[C:7]([CH:6]=1)[NH2:18])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 236145551-(4-Tert-butyl-2-nitrophenyl)-2,5-dimethylpyrrole

Product 1

HCID 540501305-Tert-butyl-2-(2,5-dimethylpyrrolyl)anilineYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A slurry of 1-(4-tert-butyl-2-nitrophenyl)-2,5-dimethylpyrrole (0.341 g, 1.25 mmol), 10% Pd/C (0.056 g) and EtOAc (50 mL) under an H2 atmosphere (balloon) was stirred for 72 h, then filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give 5-tert-butyl-2-(2,5-dimethylpyrrolyl)aniline as yellowish solids (0.30 g, 99%): TLC (10% EtOAc/90% hexane) Rf 0.43; 1H NMR (CDCl3) δ 1.28 (s, 9H), 1.87-1.91 (m, 8H), 5.85 (br s, 2H), 6.73-6.96 (m, 3H), 7.28 (br s, 1H).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-56b92c02c5014d72b100bf3d6784391f
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Reaction notes

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