4-Methyl-3-nitroanisole → 5-Methoxy-o-toluidine

HRID 1684655Notes

Reaction equation

HRID 1684655 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][C:9]=1[CH3:10])([O-])=O.[H][H]>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 871374-Methyl-3-nitroanisoleHCID 178418361HCID 178418361, compound

Product 1

HCID 995005-Methoxy-o-toluidineYield 72%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 10 gm. (60 mmol) of 3-nitro-4-methylanisole and 4 gm. of 10% Pd/C was stirred under 1 atm. of hydrogen for 30 hours, filtered, and evaporated in vacuo to give 3-amino-4-methylanisole as a residue which was dissolved in 250 ml. of tetrahydrofuran containing 13 gm. (60 mmol) of tert-butyl dicarbonate, refluxed for 3 hours, cooled, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient 5-10% Et2O /hexane to give 2 (R1=5-OMe), 10.3 gm., 72% yield, mp 72°-74° C.

Workup

  1. additionA mixture of 10 gm
  2. filtrationfiltered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3fa7bbe6c514c5d9b96ea2fe4a02d92
Source dataset
uspto-grants-1997_06
Patent number
US05641800

Reaction notes

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