4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene → 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}aniline

HRID 369388Notes

Reaction equation

HRID 369388 reaction equation
[CH3:1][C:2]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

4

Reactant 1

HCID 232857664-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene

Product 1

HCID 158701974-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}anilineYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-[5-(2,4-Dimethylbenzoyl)-1-methylpyrrol-2-ylmethyl)nitrobenzene (923 mg, 2.52 mmol) [prepared as described in Example 6, Step(e)], was dissolved in ethyl acetate (10 ml). 10% Pd/C (92 mg) was added, and the reaction mixture was vigorously stirred under hydrogen atmosphere at ambient temperature and atmospheric pressure for 2 h. The mixture was filtered through Celite®, and the filtrate was evaporated to dryness to give 4-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl-methyl)aniline (718 mg, 85%) as pale yellow crystals, mp 107.6-108.5° C.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f2caa975329b4b86a380a6845c6091ca
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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