5-Methyl-2-nitroanisole → 2-Methoxy-p-toluidine

HRID 1500804Notes

Reaction equation

HRID 1500804 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([O:8][CH3:9])[CH:7]=1.[H][H]>C1COCC1.[Pd]>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[NH2:10]

Participants

5

Reactant 2

HCID 974555-Methyl-2-nitroanisoleHCID 178418361HCID 178418361, compound

Product 1

HCID 1702192-Methoxy-p-toluidineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-methyl-2-nitroanisol (265 g, 1.58 mol) and 10% Pd/C (39.75 g) in THF (1.32 L) was stirred overnight at rt under 1 atm of hydrogen. Filtration over kieselguhr and evaporation afforded 216.1 g of the crude product which was used in the next step without further purification.

Workup

  1. filtrationFiltration
  2. customover kieselguhr and evaporation

Sources & evidence

ORD record
ord-c5d7bf044e5e4070a2c5ebc7b10d6d61
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

Loading…