[2-(5-Methoxy-2-nitrophenoxy)ethyl]dimethylamine → 2-(2-Dimethylaminoethoxy)-4-methoxyphenylamine

HRID 448364Notes

Reaction equation

HRID 448364 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:15]([O-])=O)=[C:7]([CH:14]=1)[O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:13][N:11]([CH3:12])[CH2:10][CH2:9][O:8][C:7]1[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:15]

Participants

5

Reactant 2

HCID 58307339[2-(5-Methoxy-2-nitrophenoxy)ethyl]dimethylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 189801482-(2-Dimethylaminoethoxy)-4-methoxyphenylamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [2-(5-methoxy-2-nitrophenoxy)ethyl]dimethylamine (1.2 g, 5.0 mmol) and 5% Pd—C (0.3 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 0.94 g of the product, in 90% yield: 1H NMR (CDCl3) δ 2.34 (s, 6H), 2.75 (t, J=5.8 Hz, 2H), 3.74 (s, 3H), 4.08 (t, J=5.8 Hz, 2H), 6.36 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.47 (d, J=2.5 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-875a10973c814985a922feccde414adc
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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