1-Isopropenyl-4,5-dimethoxy-2-nitro-benzene → 2-Isopropyl-4,5-dimethoxy-phenylamine

HRID 1691845Notes

Reaction equation

HRID 1691845 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[N+:14]([O-])=O)([CH3:3])=[CH2:2].[H][H]>CO.[Pd]>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH2:14])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 593778431-Isopropenyl-4,5-dimethoxy-2-nitro-benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 593777862-Isopropyl-4,5-dimethoxy-phenylamineYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Isopropenyl-4,5-dimethoxy-2-nitro-benzene (446 mg, 2.0 mmol) was dissolved in 50 ml of methanol at room temperature. 10% Palladium on Carbon (200 mg) was added and the mixture was stirred under a balloon of hydrogen overnight. The mixture was filtered through celite. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography (4:1 Hexanes/Ethyl Acetate) to give 2-isopropyl-4,5-dimethoxy-phenylamine (369 mg, 94.6%) as a tan oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (4:1 Hexanes/Ethyl Acetate)

Sources & evidence

ORD record
ord-7b81a56b03574d86a66aab52514dfd35
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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