Ethanol → 5-Methoxy-o-toluidine

HRID 547953Notes

Reaction equation

HRID 547953 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].[CH2:13](O)C>[Pd]>[CH3:13][C:6]1[CH:7]=[CH:2][C:3]([O:11][CH3:12])=[CH:4][C:5]=1[NH2:8]

Participants

4

Reactant 2

HCID 702EthanolHCID 83159Benzene, 2-methoxy-1-methyl-4-nitro-

Product 1

HCID 995005-Methoxy-o-toluidineYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a suspension of 2-methyl-5-nitroanisole F1 (1.54 g; 9.21 mmol) in absolute ethanol (15 mL) was added 10% Pd/C catalyst (249 mg). The suspension was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 6.5 h. The reaction mixture was filtered through a Millex 0.45 micron filter and evaporated to dryness to provide 4-methyl-m-anisidine F2 (1.22 g; 8.89 mmol; 97% yield)

Workup

  1. customat atmospheric pressure and room temperature
  2. customfor 6.5 h
  3. filtrationThe reaction mixture was filtered through a Millex 0.45 micron
  4. filtrationfilter
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-99232cacac96450bbe931e433b7c0ef4
Source dataset
uspto-grants-2011_05
Patent number
US07939667B2

Reaction notes

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