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

HRID 547946

Reaction equation

HRID 547946 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]>C(O)C.[Pd]>[CH3:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 785542-Methyl-3-nitroanisole

Product 1

HCID 118048223-Methoxy-2-methylanilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-3-nitro anisole A1 (5.1 g; 30.33 mmol; requires ˜30 min to dissolve) in absolute ethanol (85 mL) was added 10% Pd/C catalyst (500 mg). The solution was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 19 h. The reaction mixture was filtered through a Celite pad, rinsed and evaporated to dryness to obtain 2-methyl-3-methoxyaniline A2 as a deep mauve oil (4.1 g; 29.81 mmol; 98% yield).

Workup

  1. customat atmospheric pressure and room temperature
  2. customfor 19 h
  3. filtrationThe reaction mixture was filtered through a Celite pad
  4. washrinsed
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-caec5b9db69a44cca690ce105e1bc25d
Source dataset
uspto-grants-2011_05
Patent number
US07939667B2

Linked notes

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