2,2-Dimethyl-6-nitro-2H,4H-1,3-benzodioxin-4-one → 6-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 2098396Notes

Reaction equation

HRID 2098396 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9](=[O:15])[C:8]=2[CH:16]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[O:10][C:9](=[O:15])[C:8]=2[CH:16]=1

Participants

4

Reactant 1

HCID 597024542,2-Dimethyl-6-nitro-2H,4H-1,3-benzodioxin-4-one

Product 1

HCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-oneYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

6-Nitro-2,2-dimethyl-4H-benzo[1,3]dioxin-4-one (5 g, 22.42 mmol) was taken up in EtOH (35 ml) and 10% Pd on C (wet basis) (2.37 g) was added. The mixture was hydrogenated at 50 psi for 1 hr. The mixture was filtered through celite and the volatiles were removed in vacuo. IPA (50 ml) was added and the mixture was heated at 60° C. for 5 mins then allowed to cool to RT. The resulting solid was filtered off, washed with MTBE and dried in vacuo to give 2.93 g of 6-amino-2,2-dimethyl-4H-benzo[1,3]dioxin-4-one (68%) as a yellow solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe volatiles were removed in vacuo
  3. additionIPA (50 ml) was added
  4. temperatureto cool to RT
  5. filtrationThe resulting solid was filtered off
  6. washwashed with MTBE
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a35a2b678b4046cf97ccc95c9ab50d34
Source dataset
uspto-grants-2013_05
Patent number
US08450506B2

Reaction notes

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