Potassium Carbonate → N-Amino-3-chloro-1H-indole

HRID 233124Notes

Reaction equation

HRID 233124 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[NH2:19]OS(O)(=O)=O>CN(C=O)C>[NH2:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([Cl:1])=[CH:3]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acid3×HCID 1777903-Chloro-1H-indole

Product 1

HCID 9964198N-Amino-3-chloro-1H-indoleYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 12.6 g of 3-chloroindole in 125 ml of dry DMF at 0° C. was added 0.5 g of milled K2CO3 in 20 ml of dry DMF, followed by 30 g of KOH in 20 ml of dry DMF. The mixture was cooled to about 0° C. after which was added 13.3 g of NH2OSO3H such that the temperature did not rise above 0° C. When addition was complete, a second charge of 2.22 g of NH2OSO3H was added. When addition was complete a third 2.22 g charge of NH2OSO3H was added. The mixture was poured into ice/water/toluene, extracted into toluene, washed with water and concentrated to provide 5.6 g of an oil which crystallized on standing overnight.

Workup

  1. customdid not rise above 0° C
  2. additionWhen addition
  3. additionwas added
  4. additionWhen addition
  5. additionwas added
  6. extractionextracted into toluene
  7. washwashed with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1b298011051448b9bb1dd86a4263674e
Source dataset
uspto-grants-1997_01
Patent number
US05591866

Reaction notes

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