HCID 18542531, compound → 5-Amino-2,3-dihydro-1H-1-benzothiophene-1,1-dione

HRID 658444Notes

Reaction equation

HRID 658444 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8](=[O:12])(=[O:11])[CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-])=O>[Pd].CCO.C1COCC1>[O:11]=[S:8]1(=[O:12])[CH2:9][CH2:10][C:6]2[CH:5]=[C:4]([NH2:1])[CH:14]=[CH:13][C:7]1=2

Participants

4

Reactant 1

HCID 18542531HCID 18542531, compound

Product 1

HCID 441222605-Amino-2,3-dihydro-1H-1-benzothiophene-1,1-dioneYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent2×

Procedure

Palladium on carbon (25 mg) was placed under an inert atmosphere and suspended in 1:1 v/v EtOH/THF (10 mL). A solution of 5-nitrobenzo[b]thiophene 1,1-dioxide (250 mg, 1.18 mmol) in EtOH/THF (1:1) was then added, and the reaction mixture placed under H2 atmosphere (1 Atm pressure) and stirred at RT for 3 h. Reaction is filtered through a Celite pad and washed well with MeOH to obtain the title compound (200 mg, 92%) as a brown solid: TLC (10% MeOH/DCM w/5% NH4OH), Rf=0.40; LC MS m/z 184.1 (MH+).

Workup

  1. customReaction
  2. filtrationis filtered through a Celite pad
  3. washwashed well with MeOH

Sources & evidence

ORD record
ord-fae8050d67014c06bfde0fab466381bd
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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