4-Chloro-1,2-diaminobenzene → 6-Chloroquinoxaline-2,3-diamine

Participants

Reaction Steps

A solution of dimethyl oxaldiimidate (48 parts) in methanol (80 parts) was added to a slurry of 4-chloro-o-phenylenediamine (56 parts) in 0.3% aqueous hydrochloric acid (60 parts). The temperature rose to 54°. The reaction mixture was cooled and filtered to give a brown solid. After washing with THF, 61.4 parts of tan solid remained (80%). Recrystallization from THF or dioxane gave light-yellow crystals of 6-chloro-2,3-diaminoquinoxaline, m.p. 300°-303°.

Provenance & Evidence