N,N-dimethyl-2-(4-nitrophenoxy)ethanamine → 4-[2-(Dimethylamino)ethoxy]aniline

HRID 448377Notes

Reaction equation

HRID 448377 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 887421N,N-dimethyl-2-(4-nitrophenoxy)ethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 64846554-[2-(Dimethylamino)ethoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of dimethyl-[2-(4-nitro-phenoxy)-ethyl]-amine (3.0 g, 14 mmol) and 5% Pd—C (0.4 g) in ethyl acetate (70 mL) was hydrogenated under 50 psi hydrogen for 20 hours. The mixture was filtered through Celite and the filtrate was evaporated in vacuo, providing 2.6 g, in quantitative yield; 1H NMR (CDCl3) δ 2.32 (s, 6H), 2.69 (t, J=5.8 Hz, 2H), 3.99 (t, J=5.8 Hz, 2H), 6.00-6.66 (m, 2H), 6.73-6.78 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customproviding 2.6 g

Sources & evidence

ORD record
ord-b6fada2c26c445e7aee0ad12bfca45bc
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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