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

HRID 1744780Notes

Reaction equation

HRID 1744780 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 1

HCID 871374-Methyl-3-nitroanisole

Product 1

HCID 995005-Methoxy-o-toluidineYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

4-Methyl-3-nitroanisole (38, 5.40 g, 32.3 mmol) and Pd/C (0.50 g, 10% activated) were combined in 200 mL of MeOH and stirred under a hydrogen atmosphere (1 atm) for 60 h. Additional portions of Pd/C (0.5 g) were added after 12 and 36 h. The reaction mixture was filtered through celite to give a dark yellow oil after solvent removal. Flash chromatography silica (4:1 hexanes/EtOAc) yielded the product as a light brown solid (3.70 g, 83.5%). TLC Rf=0.27 (4:1 hexanes/EtOAc). 1H NMR (CDCl3, 500 MHz) δ2.24 (3 H, s), 3.86 (2 H, s), 3.87 (3 H, s), 6.42 (1 H, d J=2.5 Hz), 6.49 (1 H, dd, J=2.5, 8.0 Hz), 7.12 (1 H, d, J=8.5 Hz). 13C NMR (CDCl3, 125 MHz) δ15.96, 54.53, 100.38, 103.02, 114.29, 130.59, 145.61, 158.61. HRMS (EI): Calcd for M+, 137.0941; Found 137.0835.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customto give a dark yellow oil
  3. customafter solvent removal

Sources & evidence

ORD record
ord-36cf6f71551b4d29beabe23b55c838ff
Source dataset
uspto-grants-2006_03
Patent number
US07018840B2

Reaction notes

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