Benzene, 2-methoxy-1-methyl-4-nitro- → 3-Methoxy-4-methylaniline

HRID 1269528Notes

Reaction equation

HRID 1269528 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12]>[Pd].C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

4

Reactant 1

HCID 83159Benzene, 2-methoxy-1-methyl-4-nitro-

Product 1

HCID 278823-Methoxy-4-methylanilineYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A 500 mL Parr bottle was charged with 2.0 g of 10% palladium on carbon (50% water) and covered with 50 mL ethanol. 2-methyl-5-nitroanisole (10.0 g, 59.8 mmol) was dissolved in 100 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 50 psi for 3 h. The catalyst was filtered through a celite plug. The filter cake was washed with 150 mL ethanol and the filtrated concentrated under reduced pressure to yield 8.05 g (98%) of 5-amino-2-methylanisole as a clear oil.

Workup

  1. additionadded to the catalyst suspension
  2. filtrationThe catalyst was filtered through a celite plug
  3. washThe filter cake was washed with 150 mL ethanol
  4. concentrationthe filtrated concentrated under reduced pressure

Sources & evidence

ORD record
ord-b43f587a09fd4a5f90d99a21c3f647b0
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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