4-(1-Methylpyrrol-2-ylmethyl)nitrobenzene → 4-(1-Methylpyrrol-2-yl-methyl)aniline

HRID 365629Notes

Reaction equation

HRID 365629 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 232857944-(1-Methylpyrrol-2-ylmethyl)nitrobenzene

Product 1

HCID 232859674-(1-Methylpyrrol-2-yl-methyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(1-Methylpyrrol-2-ylmethyl)nitrobenzene (500 mg, 2.31 mmol) [prepared as described in Example 21, Step (b)], was dissolved in ethyl acetate and subjected to hydrogenation over 5% Pd/C (50 mg) at ambient temperature and atmospheric pressure. After 3 h the mixture was filtered and the filtrate was concentrated to give 4-(1-methylpyrrol-2-yl-methyl)aniline (430 mg, 100%) as a yellow oil. ##STR63##

Workup

  1. filtrationAfter 3 h the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7750102a0099436c9283fccd80d31ac0
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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