4-Nitro-2,3,6-trimethylanisole → 4-Methoxy-2,3,5-trimethylaniline

HRID 2103062Notes

Reaction equation

HRID 2103062 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([N+:11]([O-])=O)=[CH:5][C:4]=1[CH3:14]>C(OC(=O)C)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([NH2:11])=[C:7]([CH3:10])[C:8]=1[CH3:9]

Participants

4

Reactant 1

HCID 224085124-Nitro-2,3,6-trimethylanisole

Product 1

HCID 147002344-Methoxy-2,3,5-trimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxy-1,3,4-trimethyl-5-nitrobenzene (2.3 g) from the step above, was dissolved in 250 mL ethylacetate, to which Pd/C (0.6 g) was added. House vacuum was applied to it and then it was flushed with hydrogen. This cycle was repeated three times. The suspension was kept at room temperature with a hydrogen balloon overnight. The suspension was then filtered through a pad of Celite® and evaporated to dryness. Elution on a silicagel column (DCM: EtOAc, 10:1-5:1) gave 4-methoxy-2,3,5-trimethylaniline as a solid with slight pink color (0.9 g). 1H-NMR (300 MHz, CDCl3), δ=6.4 (s, 1H), 3.631 (s, 3H), 3.392 (br s, 2H), 2.202 (s, 6H), 2.046 (s, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=149.73, 140.35, 129.85, 128.36, 119.92, 115.17, 60.33, 16.02, 13.24, 12.83 ppm.

Workup

  1. additionwas added
  2. customit was flushed with hydrogen
  3. customwas kept at room temperature with a hydrogen balloon overnight
  4. filtrationThe suspension was then filtered through a pad of Celite®
  5. customevaporated to dryness
  6. washElution on a silicagel column (DCM: EtOAc, 10:1-5:1)

Sources & evidence

ORD record
ord-39ad000ad9b3404a90b2ec6f48f1cfd9
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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