Ethanol → HCID 86744472, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitro-3-fluoropyridine N-oxide (5.4 g) and 5-amino-2-methylindole (5.0 g) in 100 mL of thoroughly degassed absolute ethanol was stirred at 50° C. for 30 minutes and then cooled slowly to 0° C. The precipitate was collected and air dried to give 9.0 g of N-(4-nitro-3-pyridinyl)-2-methyl-1H-indol-5-amine N5 -oxide as a powder. This powder was taken up in 135 mL of isopropanol and hydrogenated at 50° C. over 3% platinum on carbon at 50 psi in the presence of lithium hydroxide (0.26 g). Filtration and concentration left 8.0 g of a solid which was recrystallized from 32 mL of methanol giving 4.9 g of crystals. This material was then azeotroped repeatedly with absolute ethanol and dried at 85° C. to give 2.4 g of crystals, mp=96°-98° C.

Provenance & Evidence