6-Nitro-5,8-dimethyl-1,4-benzodioxane → 6-Amino-5,8-dimethyl-1,4-benzodioxane

HRID 1376551Notes

Reaction equation

HRID 1376551 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([CH3:14])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]=1[CH3:15])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:13]=[C:12]([CH3:14])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]=1[CH3:15]

Participants

5

Reactant 2

HCID 218404806-Nitro-5,8-dimethyl-1,4-benzodioxaneHCID 178418361HCID 178418361, compound

Product 1

HCID 218404886-Amino-5,8-dimethyl-1,4-benzodioxaneYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.10 g of 6-nitro-5,8-dimethyl-1,4-benzodioxane and 0.30 g of 10% palladium on carbon in 75 mL of ethanol is placed under a 50 psi hydrogen atmosphere. The mixture is shaken for three hours at room temperature. The reaction mixture is filtered through Celite to yield a brownish solution. Concentration under reduced pressure affords 2.6 g of 6-amino-5,8-dimethyl-1,4-benzodioxane.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customto yield a brownish solution
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-deaea483adb946899b87862d5d86862b
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

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