4-Methoxy-5-methyl-2-nitrophenol → 2-Amino-4-methoxy-5-methylphenol

HRID 2114356Notes

Reaction equation

HRID 2114356 reaction equation
[CH3:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1>CCOC(C)=O.[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([O:12][CH3:13])[C:2]([CH3:1])=[CH:7][C:6]=1[OH:8]

Participants

4

Reactant 1

HCID 574186644-Methoxy-5-methyl-2-nitrophenol

Product 1

HCID 130767582-Amino-4-methoxy-5-methylphenolYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-4-(methyloxy)-2-nitrophenol (3.65 g, 20 mmol) was dissolved in EtOAc (100 mL) and 200 mg of 5% Pd/C was added. The reaction vessel was evacuated and filled with N2. This process was repeated twice then filled with H2 at 1 atm, and stirred for 16 h. The mixture was filtered through a pad of celite, washed with EtOAc, and the solvent was removed via rotovap to give the title compound (3.0 g, 98%) as a white solid. MS (ES) m/e 154 [M+H]+.

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with N2
  3. additionThis process was repeated twice then filled with H2 at 1 atm
  4. filtrationThe mixture was filtered through a pad of celite
  5. washwashed with EtOAc
  6. customthe solvent was removed via rotovap

Sources & evidence

ORD record
ord-0801897b26b04a3eacc143492504e88a
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

Loading…