4-Methoxy-1-nitro-2-phenoxybenzene → 4-Methoxy-2-phenoxyaniline

HRID 448384Notes

Reaction equation

HRID 448384 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 583072504-Methoxy-1-nitro-2-phenoxybenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 583072004-Methoxy-2-phenoxyanilineYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture 4-methoxy-1-nitro-2-phenoxy-benzene (1.3 g, 5.3 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (100 mL) was shaken under 50 psi of hydrogen for 20 hours. The mixture was filtered through Celite and evaporated, providing 1.1 g of the product as a light gold oil; 1H NMR (CDCl3) δ 3.70 (s, 3H), 6.49 (d, J=2.6 Hz, 1H), 6.59 (dd, J=8.6 Hz, J=2.6 Hz, 1H), 6.78 (d, J=8.6 Hz, 1H), 6.96-7.00 (m, 2H), 7.07 (t, J=7.3 Hz, 1H), 7.28-7.35 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-71e41d6902e34dd3b5241e2c1395faad
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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