1-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine → 4-((Dimethylamino)methyl)-2-methoxyaniline

HRID 448370Notes

Reaction equation

HRID 448370 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[CH2:6][N:7]([CH3:9])[CH3:8].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:9][N:7]([CH2:6][C:5]1[CH:10]=[CH:11][C:12]([NH2:13])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:8]

Participants

5

Reactant 2

HCID 220464651-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 220462864-((Dimethylamino)methyl)-2-methoxyanilineYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3-methoxy-4-nitrobenzyl)dimethylamine (1.5 g, 7.1 mmol) and 5% Pd—C (0.2 g) in ethyl acetate (75 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 1.2 g of the product as a light grey oil, in 93% yield: 1H NMR (CDCl3) δ 2.22 (s, 6H), 3.32 (s, 2H), 3.74 (br, 2H), 3.86 (s, 3H), 6.62-6.67 (m, 2H), 6.78 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-9345d9c42b104a7394264edc5aa37532
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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