HCID 57585844, compound → HCID 57585850, compound

HRID 547615Notes

Reaction equation

HRID 547615 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[O:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(OC(=O)C)C.[Pd]>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:15]1[CH:16]=[CH:17][C:12]([O:11][C:4]2[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([CH3:1])[CH:3]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 57585844HCID 57585844, compound

Product 1

HCID 57585850HCID 57585850, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 500 mL round bottom flask containing 2-{4-[(3-methyl-4-nitrophenyl)oxy]phenyl}-1,3-dioxolane (1.89 g, 6.27 mmol) in 60 mL ethylacetate was purged with nitrogen gas and treated with 10% palladium on carbon (650 mg, 0.63 mmol). A balloon with H2 gas was attached and gas was allowed to bubble through the solution while allowing gas to escape the flask via needle. The needle was removed, and the reaction stirred under H2 atmosphere for 2 days. The reaction was filtered through Celite, concentrated and purified via silica gel column chromatography (0% to 100% ethylacetate/hexane gradient) to provide 1.24 g 4-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-2-methylaniline.

Workup

  1. customwas purged with nitrogen gas
  2. customto bubble through the solution
  3. customThe needle was removed
  4. filtrationThe reaction was filtered through Celite
  5. concentrationconcentrated
  6. custompurified via silica gel column chromatography (0% to 100% ethylacetate/hexane gradient)

Sources & evidence

ORD record
ord-7b343e8b4ce545178ceb8d67d2d3bbda
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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