HCID 11210335, compound → HCID 11347838, compound

HRID 1006412Notes

Reaction equation

HRID 1006412 reaction equation
[C:1]1([S:11]([N:14]2[C:22]3[C:17](=[C:18]([N+:23]([O-])=O)[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)C.CO>[C:1]1([S:11]([N:14]2[C:22]3[C:17](=[C:18]([NH2:23])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 11210335HCID 11210335, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11347838HCID 11347838, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 722 mg (1.97 mmole) 1-(naphthalene-1-sulfonyl)-4-nitro-1H-indole and 100 mg 10% palladium on carbon in 15 mL ethanol and 5 mL methanol was shaken under 40 psi hydrogen at room temperature for 4 hrs. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ether/hexane to provide 1-(naphthalene-1-sulfonyl) -1H-indol-4-ylamine as light yellow-green crystals, 480 mg, m.p. 133-134° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-7105149d2e0d4027860cd8105d77f7af
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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