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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence