Sodium Hydroxide → HCID 11210335, compound

HRID 1006411Notes

Reaction equation

HRID 1006411 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[OH-].[Na+].[C:15]1([S:25](Cl)(=[O:27])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:15]1([S:25]([N:8]2[C:9]3[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)(=[O:27])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 665601-Naphthalenesulfonyl chlorideHCID 1457664-Nitro-1H-indole

Product 1

HCID 11210335HCID 11210335, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 370 mg (2.3 mmole) 4-nitro-1H-indole in 10 mL toluene was added 5 mL 4 M sodium hydroxide and 50 mg tetra-n-butyl ammonium hydrogen sulfate. Solid naphthalene-1-sulfonyl chloride (533 mg, 2.35 mmole) was added in one portion. The reaction mixture was stirred at room temperature for 0.25 hr. The mixture was diluted with 5 mL water and extracted with 25 mL ethyl ether. The organic phase was washed with 5 mL water, 5 mL saturated sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ether/hexane to provide 1-(naphthalene-1-sulfonyl)-4-nitro-1H-indole as light yellow crystals, 779 mg, m.p. 156-157° C.

Workup

  1. extractionextracted with 25 mL ethyl ether
  2. washThe organic phase was washed with 5 mL water, 5 mL saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-948dab3452c54f9fb7076bd64e0f1962
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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