Hydrochloric Acid → 1-(Phenylsulfonyl)-1H-indol-5-ol

HRID 1159827Notes

Reaction equation

HRID 1159827 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]2)C1C=CC=CC=1.C1CCCCC=1.Cl>CCO.[Pd]>[C:21]1([S:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)(=[O:19])=[O:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 118246245-(Phenylmethoxy)-1-phenylsulfonylindole2×

Product 1

HCID 99705131-(Phenylsulfonyl)-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-(benzyloxy)-1-(phenylsulfonyl)-1H-indole (0.50 g, 1.37 mmol; Intermediate 86) in EtOH (3 mL), Pd/C (30 wt %, 0.15 g), cyclohexene (1 mL), and HCl (1 mL) and was added. The reaction mixture was warmed to 150° C. for 1 h using microwave heating. The Pd/C was filtered off and the solvent was removed under reduced pressure. The product (about 95% pure) was used without further purification.

Workup

  1. temperatureheating
  2. filtrationThe Pd/C was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customThe product (about 95% pure) was used without further purification

Sources & evidence

ORD record
ord-71196dfddf07459baa055b1f2230c353
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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