4-methyl-3-nitro-N,N-dipropylaniline → 4-Methyl-N1,N1-dipropyl-benzene-1,3-diamine

HRID 2235507Notes

Reaction equation

HRID 2235507 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([N:6]([CH2:10][CH2:11][CH3:12])[CH2:7][CH2:8][CH3:9])=[CH:4][C:3]=1[N+:15]([O-])=O>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([N:6]([CH2:10][CH2:11][CH3:12])[CH2:7][CH2:8][CH3:9])=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 1

HCID 685817644-methyl-3-nitro-N,N-dipropylaniline

Product 1

HCID 629129824-Methyl-N1,N1-dipropyl-benzene-1,3-diamineYield 31.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methyl-3-nitro-N,N-dipropylaniline (2.49 g, 10.5 mmol) and 10% Pd on carbon (1.00 g) in AcOEt (50 ml) was hydrogenated for 18 h. The catalyst was removed by filtration through Celite. The filtrate was concentrated under vacuum. The residue was purified by chromatography eluting with 10% AcOEt in n-hexane to afford 689 mg of the title compound.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customThe residue was purified by chromatography
  4. washeluting with 10% AcOEt in n-hexane

Sources & evidence

ORD record
ord-27324cd247b34055bf4428f7805ae637
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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