Hydrochloric Acid → 6-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-1H-indole

HRID 1475322Notes

Reaction equation

HRID 1475322 reaction equation
[CH2:1]([S:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:19])([CH3:18])[CH2:11][N:12]2C(=O)C)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].Cl>CO>[CH2:1]([S:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:18])([CH3:19])[CH2:11][NH:12]2)=[CH:8][CH:7]=1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 709808661-(6-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

Product 1

HCID 867239446-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-1H-indoleYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

1-(6-Ethanesulfonyl-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (130 mg, 0.46 mmol) was dissolved in MeOH (7 mL) and 5 M hydrochloric acid (920 μL, 4.6 mmol) was added. The solution was stirred at 90° C. for 1.5 h then solvent was removed in vacuo. The residue was quenched with saturated aqueous NaHCO3 and the product extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (60 mg), used without further purification. MS: [M+H]+=240.

Workup

  1. customsolvent was removed in vacuo
  2. customThe residue was quenched with saturated aqueous NaHCO3
  3. extractionthe product extracted with EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcc0d8f9ef264edf84cee1e2bd8622bf
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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