Anisole → HCID 353540, compound

HRID 905534Notes

Reaction equation

HRID 905534 reaction equation
C1(OC)C=CC=CC=1.[N+:9]([C:12]1[CH:28]=[CH:27][C:15]2[O:16][C:17]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:18]=3[O:19][C:14]=2[CH:13]=1)([O-])=O.[H][H]>[Pd].C1COCC1>[NH2:24][C:22]1[CH:21]=[CH:20][C:18]2[O:19][C:14]3[CH:13]=[C:12]([NH2:9])[CH:28]=[CH:27][C:15]=3[O:16][C:17]=2[CH:23]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 1501562,7-Dinitrodibenzo-p-dioxinHCID 178418361HCID 178418361, compound

Product 1

HCID 353540HCID 353540, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1200 ml of anisole and 800 ml of THF were added 69.7 g (0.254 mole) of 2,7-dinitrodibenzodioxin and 22.2 g of 10% palladium/carbon and hydrogen gas was passed through the mixture with stirring at room temperature for 8 hours. The 10% palladium/carbon was removed by filtration, then a precipitate containing the 10% palladium/carbon was collected by filtration, and the precipitate was rinsed with THF. The rinsings were concentrated and dried under reduced pressure to give 25.0 g (0.117 mole, 46.0% yield) of 2,7-diaminodibenzodioxin. The product showed a purity of 98.1% (HPLC, 254 nm).

Workup

  1. customThe 10% palladium/carbon was removed by filtration
  2. additiona precipitate containing the 10% palladium/carbon
  3. filtrationwas collected by filtration
  4. washthe precipitate was rinsed with THF
  5. concentrationThe rinsings were concentrated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-21d6ba9caca04c3f9bbb3f352b77d03a
Source dataset
uspto-grants-2011_09
Patent number
US08012606B2

Reaction notes

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