HCID 57678416, compound → HCID 57678438, compound

HRID 491507Notes

Reaction equation

HRID 491507 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([NH2:12])=[CH:6][C:5]=1[O:13][CH3:14])([CH3:3])=[CH2:2]>C(O)C.[Pd]>[CH:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([NH2:12])=[CH:6][C:5]=1[O:13][CH3:14])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57678416HCID 57678416, compound

Product 1

HCID 57678438HCID 57678438, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-Isopropenyl-3,5-dimethoxy-phenylamine (take directly from step 5) in ethanol (200 mL) was hydrogenated overnight at room temperature and 1 psig of H2 gas using 10% palladium on charcoal catalyst (200 mg). The reaction was filtered through Celite and the pad was washed with additional ethanol. Concentration of the filtrate and purification by silica gel column chromatography eluting with 70/30 hexane/ethyl acetate yielded 4-Isopropyl-3,5-dimethoxy-phenylamine (1.4 g, 69%) as a pale pink solid, MS (M+H)=196.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washthe pad was washed with additional ethanol
  3. customConcentration of the filtrate and purification by silica gel column chromatography
  4. washeluting with 70/30 hexane/ethyl acetate

Sources & evidence

ORD record
ord-1a55aebe592e4db58ae1d33bd7495e8d
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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