Reaction #992716

Reaction equation

anisole

2,7-dinitrodibenzodioxin

hydrogen

→

2,7-diaminodibenzodioxin

Yield 46.1%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe 10% palladium/carbon was removed by filtration
2. 2
   workup.ADDITIONa precipitate containing the 10% palladium/carbon
3. 3
   Filtrationwas collected by filtration
4. 4
   Washthe precipitate was rinsed with THF
5. 5
   ConcentrationThe rinsings were concentrated
6. 6
   Otherdried under reduced pressure

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).

Source