Ammonium formate → 3(2H)-Benzofuranone, 5-amino-2,2,6,7-tetramethyl-

HRID 1787104Notes

Reaction equation

HRID 1787104 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6](=[O:7])[C:5]2[CH:8]=[C:9]([N+:14]([O-])=O)[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]2[O:3][C:2]([CH3:1])([CH3:17])[C:6](=[O:7])[C:5]=2[CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 231138962,2,6,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-one

Product 1

HCID 231141353(2H)-Benzofuranone, 5-amino-2,2,6,7-tetramethyl-Yield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,2,6,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-one obtained in Reference Example 46 (5.0 g, 21.3 mmol), 10%-palladium carbon (50% hydrous, 500 mg) and ammonium formate (7.06 g, 85.0 mmol) in methanol (100 mL) was heated under reflux for two hours. The solid material was removed and the filtrate was concentrated under reduced pressure. Water and ethyl acetate were added to the residue to separate the organic layer, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The solvent was distilled off under reduced pressure to obtain a residue, which was crystallized with ethyl acetate-hexane to obtain 4.0 g (yield 92%) of the title compound. Melting point: 149-150° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. customThe solid material was removed
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater and ethyl acetate were added to the residue
  6. customto separate the organic layer
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. distillationThe solvent was distilled off under reduced pressure
  12. customto obtain a residue, which
  13. customwas crystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-bf5133e21aff459ca5e01da7ef38cae1
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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