Tetrahydrofuran → 5-Aminoindole

HRID 1359134Notes

Reaction equation

HRID 1359134 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-])=O.O1CCCC1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 225235-NitroindoleHCID 2723923Ammonium formate

Product 1

HCID 788675-AminoindoleYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-nitroindole (1.0 g, 6.17 mmol) was dissolved in methanol (10 ml) and anhydrous tetrahydrofuran (10 ml) at room temperature and then, palladium/carbon (10%) of a catalystic amount and ammonium formate (2.0 g, 31.7 mmol) were added to be stirred slowly at room temperature for 30 minutes. After completing the reaction, the reacting solution was filtered through celite, washed with methanol, concentrated under reduced pressure and then, dropped a silica gel short column. Afterward, the residue was concentrated again under reduced pressure and triturated with isooctane. As a result, the present compound (0.45 g, productive yield 55%) was obtained as a solid phase.

Workup

  1. customthe reaction
  2. filtrationthe reacting solution was filtered through celite
  3. washwashed with methanol
  4. concentrationconcentrated under reduced pressure
  5. additiondropped a silica gel short column
  6. concentrationAfterward, the residue was concentrated again under reduced pressure
  7. customtriturated with isooctane
  8. customAs a result, the present compound (0.45 g, productive yield 55%) was obtained as a solid phase

Sources & evidence

ORD record
ord-1f887c7bbff94cb291f63c751cc84db2
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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