Indole → 1-Aminoindole

HRID 1742044Notes

Reaction equation

HRID 1742044 reaction equation
C[N:2](C)C=O.[OH-].[K+].[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.NOS(O)(=O)=O>O>[NH2:2][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

6

Reactant 4

HCID 798IndoleHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 6432211-AminoindoleYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of N,N-dimethylformamide were added 24.55 g(440 mmol) of potassium hydroxide and 3.201 g(27.3 mmol) of 1H-indole, and 6.15 g (54.4 mmol) of hydroxylamine-0-sulfonic acid was added thereto in small amounts under stirring. After stirring the reaction mixture at room temperature for 1 hour, 50 ml of water was added thereto and it was extracted three times with 100 ml of benzene. The extract was washed with water, dried and concentrated under the reduced pressure. Silica gel column chromatography of the residue using 50% dichloromethane/n-hexane as an eluent gave 1.16 g of the desired compound(32%).

Workup

  1. additionwas added
  2. stirringAfter stirring the reaction mixture at room temperature for 1 hour
  3. extractionit was extracted three times with 100 ml of benzene
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-88a5128f898143849790be1c7f8dd5e0
Source dataset
uspto-grants-1994_08
Patent number
US05336673

Reaction notes

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