2-Methyl-3-nitroanisole → 3-Methoxy-2-methylaniline

HRID 1995388Notes

Reaction equation

HRID 1995388 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[CH3:12].[H][H]>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:6]=[CH:7][CH:8]=1)[NH2:9]

Participants

5

Reactant 2

HCID 785542-Methyl-3-nitroanisoleHCID 178418361HCID 178418361, compound

Product 1

HCID 118048223-Methoxy-2-methylaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

200 gm (1.19 mols) of 2-methoxy-6-nitro-toluene were hydrogenated in 2.5 liters of ethanol in the presence of 25 gm of Raney nickel at 100 bar until the absorption of the calculated amount of hydrogen. The reaction mixture was filtered and evaporated in vacuo. After distillation 158.3 gm (97% of theory) of 3-methoxy-2-methylaniline were obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. distillationAfter distillation 158.3 gm (97% of theory) of 3-methoxy-2-methylaniline
  4. customwere obtained

Sources & evidence

ORD record
ord-5afd0e1827d6400aaa1e43226f127dd0
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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