Water → HCID 59456112, compound

HRID 1672408Notes

Reaction equation

HRID 1672408 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.O>C(O)C.Cl.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 962WaterHCID 44596163HCID 44596163, compound

Product 1

HCID 59456112HCID 59456112, compoundYield 133.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 1-(3-Nitrobenzenesulfonyl)indole (6.62 mmoles, 2.0 g) in 10 mL of ethanol in 50 mL three necked round bottomed flask, was added (33.11 mmoles, 1.85 g) of iron powder at 25° C. To the above mixture was added 2 mL water and 1-2 drops of hydrochloric acid. The reaction mixture was then stirred for 4 hour at 75-80° C. After the completion of reaction (TLC), the reaction mixture was filtered through buchner funnel and residue was washed with 20 mL×2 portions of hot ethanol. Combined ethanol layer was distilled under vacuum, the residue was quenched in 30 mL ice-cold water and basified with 40% sodium hydroxide solution. Aqueous layer was extracted with dichloromethane (50 mL×3). The combined dichloromethane extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 2.4 g crude thick oil. This compound was purified on column using neutral silica and n-hexane to 40% ethylacetate:n-hexane as eluent.

Workup

  1. customAfter the completion of reaction (TLC)
  2. filtrationthe reaction mixture was filtered through buchner funnel
  3. washresidue was washed with 20 mL×2 portions of hot ethanol
  4. distillationCombined ethanol layer was distilled under vacuum
  5. customthe residue was quenched in 30 mL ice-cold water and basified with 40% sodium hydroxide solution
  6. extractionAqueous layer was extracted with dichloromethane (50 mL×3)
  7. washThe combined dichloromethane extracts were then washed with water, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe volatiles were removed under the reduced pressure

Sources & evidence

ORD record
ord-0f6de26b855844c4a78e1b614a19afc2
Source dataset
uspto-grants-2011_08
Patent number
US07998981B2

Reaction notes

Loading…