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

HRID 1850377Notes

Reaction equation

HRID 1850377 reaction equation
O1CCCC1.C([NH:13][C:14]1[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19](=[O:24])[C:18]=2[CH:25]=1)C1C=CC=CC=1>[C].[Pd].CO>[NH2:13][C:14]1[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]2[O:21][C:20]([CH3:22])([CH3:23])[C:19](=[O:24])[C:18]=2[CH:25]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66759427HCID 66759427, compound

Product 1

HCID 231141353(2H)-Benzofuranone, 5-amino-2,2,6,7-tetramethyl-Yield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

5% palladium carbon (50% water content, 9.50 g) was added to a mixed solution of tetrahydrofuran (100 mL) and methanol (100 mL) containing 5-(benzylamino)-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (9.48 g, 32.1 mmol) synthesized in Reference Example 19, and the mixture was stirred under hydrogen atmosphere at room temperature for 22 hours. Palladium carbon was removed by filtration, and then the solvent was removed under reduced pressure to give 6.59 g of the title compound (yield: 100%).

Workup

  1. customsynthesized in Reference Example 19
  2. customPalladium carbon was removed by filtration
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3ea20cfbe4264d63851c5a9641630a04
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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