N-(2-methyl-3-nitrobenzyl)-1-ethanamine → 3-[(Ethylamino)methyl]-2-methylaniline

HRID 1822867Notes

Reaction equation

HRID 1822867 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][NH:5][CH2:6][CH3:7]>CCOC(C)=O.CCO.[Pd]>[CH2:6]([NH:5][CH2:4][C:3]1[C:2]([CH3:1])=[C:11]([CH:10]=[CH:9][CH:8]=1)[NH2:12])[CH3:7]

Participants

4

Reactant 1

HCID 22170308N-(2-methyl-3-nitrobenzyl)-1-ethanamine

Product 1

HCID 221702563-[(Ethylamino)methyl]-2-methylanilineYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

N-(2-methyl-3-nitrobenzyl)-1-ethanamine (0.46 g, 2.3 mmol) was hydrogenated over 5% palladium-charcoal 80 mg in EtOAc/EtOH 1:1 (14 ml) for four hours. The mixture was filtered through celite, and the filtrate was concentrated to give the title compound 0.373 g (97%) as a pale yellow oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6d4ae3ae76904c4e9469c226600f0dc3
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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