Nitric Acid → HCID 20513345, compound

Participants

Reaction Steps

Acetylation of 6-amino-5-indanol with acetic anhydride in ethyl acetate/pyridine gives 6-acetamido-5-acetoxyindan (m.p. 157°-158° C.), reaction of which with nitric acid in acetic anhydride gives 5-acetamido-6-acetoxy-4-nitroindan (m.p. 168°-170° C.). Acid saponification of this compound with hydrochloric acid gives 6-amino-7-nitro-5-indanol (m.p. 196°-198° C.), which is then reacted with 3-chloro-1,2-epoxypropane in dilute aqueous sodium hydroxide solution to give 5-amino-6-(2,3-epoxypropoxy)-4-nitroindan in the form of a dark oil, reaction of which with tert.-butylamine gives 5-amino-6-(2-hydroxy-3-tert.-butylaminopropoxy)-4-nitroindan in the form of an amorphous hydrochloride. Hydrogenation thereof in ethanolic solution in the presence of platinum dioxide gives 4,5-diamino-6-(2-hydroxy-3-tert.-butylaminopropoxy)-indan in the form of an amorphous trihydrochloride.

Provenance & Evidence