Water → HCID 59456112, compound

HRID 1675322Notes

Reaction equation

HRID 1675322 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, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
77.5 °C

Procedure

1-(3-Nitrobenzenesulfonyl)-1H-indole (obtained from step (ii)) (6.62 mmol, 2.0 grams) was taken in ethanol (10 mL) in a 50 mL three-necked round-bottomed flask. Iron powder, (33.11 mmol, 1.85 grams) was added to it at 25° C. followed by addition of water (2 mL) and 1-2 drops of hydrochloric acid. The reaction mixture was then stirred for a period of 4 hours at 75-80° C. After completion of the reaction, the reaction mixture was filtered through buchner funnel and solid mass on the filter was washed twice with hot ethanol (20 mL). Combined ethanol layer was concentrated under vacuum and the residual mass was poured onto ice-cold water (30 mL) and basified with 40% sodium hydroxide solution. Aqueous layer was extracted with dichloromethane (50 mL×3). The combined dichloromethane extracts were washed with water, brine and dried over anhydrous magnesium sulfate. The volatile substances were then removed tinder reduced pressure to obtain 2.4 grams thick syrupy mass which was purified by column chromatography using neutral silicagel (100-200 mesh), eluent being ethyl acetate and n-hexane (2:3).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through buchner funnel
  3. washsolid mass on the filter was washed twice with hot ethanol (20 mL)
  4. concentrationCombined ethanol layer was concentrated under vacuum
  5. additionthe residual mass was poured onto ice-cold water (30 mL)
  6. extractionAqueous layer was extracted with dichloromethane (50 mL×3)
  7. washThe combined dichloromethane extracts were washed with water, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe volatile substances were then removed tinder reduced pressure
  10. customto obtain 2.4 grams thick syrupy mass which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cd3b247ff83449ff87cdb2bc43a706a4
Source dataset
uspto-grants-2011_08
Patent number
US08003670B2

Reaction notes

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