2-Ethoxy-1-methoxy-4-nitro-benzene → 3-Ethoxy-4-methoxyaniline

HRID 448336Notes

Reaction equation

HRID 448336 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 167919473-Ethoxy-4-methoxyanilineYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-ethoxy-1-methoxy-4-nitrobenzene (1.5 g, 7.6 mmol) and 5% Pd—C (0.3 g) in 30 mL of ethyl acetate was hydrogenated under 50 psi of hydrogen gas for 14 hours. The mixture was filtered through Celite and the filtrate was evaporated, providing 1.25 g of the product, in 98% yield: 1H NMR (CDCl3) δ 1.44 (t, J=7.0 Hz, 3H), 3.27 (br, 2H), 3.79 (s, 3H), 4.04 (q, J=7.0 Hz, 2H), 6.90 (d, J=8.9 Hz, 1H), 7.74 (d, J=2.5 Hz, 1H), 7.90 (dd, J=8.9 Hz, J=2.5 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9aa3d4c3541941fdb4d0c000ab4818a8
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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