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

HRID 1893668Notes

Reaction equation

HRID 1893668 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]>CCO.[Pd]>[CH3:12][O:11][C:3]1[C:2]([CH3:1])=[C:7]([CH:6]=[CH:5][CH:4]=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 2-methyl-3-nitroanisole (5.02 g, 29.9 mmol) in EtOH (300 mL) was added Pd/C (0.50 g). The reaction was stirred under a H2 balloon overnight then filtered through celite to afford 3-methoxy-2-methylaniline (4.00 g, 98%). LCMS found 138.0 [M+H]+.

Workup

  1. filtrationthen filtered through celite

Sources & evidence

ORD record
ord-4071e8248e1c405b9ded7343022bb1c3
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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