1,2,3,3-tetramethyl-2H-indol-6-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-1,2,3,3-tetramethylindoline (6.9 g, 0.036 mole) was treated with 6.8 g of ethyl trifluoroacetoacetate. There was an immediate reaction with heat evolution and formation of a solid. The mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C., then for 1 hr at 145°-150° C. The cooled cake was broken up, triturated with 10 ml of diethyl ether, filtered and washed twice with cold ether; 7.7 g (69%). When recrystallized from 275 ml of 95% ethanol, the compound was obtained as felted, yellow needles; m.p. 248°-249° C., shrinking at 244° C. an immediate reaction with heat evolution and formation of a solid The mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C. triturated with 10 ml of diethyl ether filtered washed twice with cold ether When recrystallized from 275 ml of 95% ethanol the compound was obtained shrinking at 244° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-1,2,3,3-tetramethylindoline (6.9 g, 0.036 mole) was treated with 6.8 g of ethyl trifluoroacetoacetate. There was an immediate reaction with heat evolution and formation of a solid. The mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C., then for 1 hr at 145°-150° C. The cooled cake was broken up, triturated with 10 ml of diethyl ether, filtered and washed twice with cold ether; 7.7 g (69%). When recrystallized from 275 ml of 95% ethanol, the compound was obtained as felted, yellow needles; m.p. 248°-249° C., shrinking at 244° C. an immediate reaction with heat evolution and formation of a solid The mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C. triturated with 10 ml of diethyl ether filtered washed twice with cold ether When recrystallized from 275 ml of 95% ethanol the compound was obtained shrinking at 244° C.