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

HRID 527719Notes

Reaction equation

HRID 527719 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]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

3

Reactant 1

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

Product 1

HCID 278823-Methoxy-4-methylanilineYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-2-(methyloxy)-4-nitrobenzene (2.5 g, 14.96 mmol) in methanol (50 mL) Ni-Raney (˜2 g) was added and the reaction mixture was stirred overnight at room temperature under H2 atmosphere (1 atm). The catalyst was filtered off and the residue was purified by SCX cartridge (50 g) to afford the title compound (1.86 g) as a colourless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe residue was purified by SCX cartridge (50 g)

Sources & evidence

ORD record
ord-f265de6e7e6f4015b51a458380e9583b
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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