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

HRID 1593027Notes

Reaction equation

HRID 1593027 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)(=O)C.C(OCC)(=O)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 121.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-nitro-1-benzothiophene 1,1-dioxide (1.04 g) in acetic acid (50 ml) and ethyl acetate (50 ml) was hydrogenated over (10% palladium on carbon (130 mg, 50% wet). The catalyst was removed by filtration and washed with ethyl acetate. The filtrate and washings were evaporated under reduced pressure to give the title compound (1.1 g). LCMS RT=1.50 min

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. customThe filtrate and washings were evaporated under reduced pressure

Sources & evidence

ORD record
ord-06bafa995bcd4514b6ac26f4e65360e1
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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