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

HRID 1096586Notes

Reaction equation

HRID 1096586 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-c96738f321c342cda658c33419e43450
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

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