4-Methyl-3-nitroanisole → 5-Methoxy-o-toluidine

HRID 544725

Reaction equation

HRID 544725 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O>CO.[Pd]>[NH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 871374-Methyl-3-nitroanisole

Product 1

HCID 995005-Methoxy-o-toluidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

12.4 g of palladium-on-carbon are added to a solution of 132.9 g (0.759 mole) of 4-methyl-3-nitro-anisole in 1.1 liters of methanol and hydrogenation is carried out at room temperature. The catalyst is filtered off and the filtrate is concentrated in a vacuum rotary evaporator. Recrystallisation from isopropanol/water yields 3-amino-4-methylanisole having a melting point of 43°-44°.

Workup

  1. customis carried out at room temperature
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in a vacuum rotary evaporator
  4. customRecrystallisation from isopropanol/water

Sources & evidence

ORD record
ord-6c3bae7188a248158e890e52b408fc42
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Linked notes

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