Stattic → 6-Amino-2,3-dihydro-1lambda6-benzothiophene-1,1-dione

HRID 554247Notes

Reaction equation

HRID 554247 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH:8]=[CH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=1)([O-])=O>C(O)C.CO.[C].[Pd]>[S:10]1(=[O:11])(=[O:12])[C:6]2[CH:5]=[C:4]([NH2:1])[CH:14]=[CH:13][C:7]=2[CH2:8][CH2:9]1

Participants

5

Reactant 1

HCID 2779853Stattic

Product 1

HCID 122853256-Amino-2,3-dihydro-1lambda6-benzothiophene-1,1-dioneYield 75%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a suspension of 6-nitro-1-benzothiophene 1,1-dioxide (2.02 g) in ethanol (200 mL) and methanol (60 mL) was added 10% palladium carbon (50% containing water, 265 mg), and the mixture was stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound as a white solid (yield 1.31 g, 75%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3c6dba7a4c0b4132991e4fa0de208d40
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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