Nitric Acid → HCID 20513345, compound

HRID 1163902Notes

Reaction equation

HRID 1163902 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[O:14][C:15](=[O:17])[CH3:16])(=[O:3])[CH3:2].[N+:18]([O-])([OH:20])=[O:19]>C(OC(=O)C)(=O)C>[C:1]([NH:4][C:5]1[C:13]([N+:18]([O-:20])=[O:19])=[C:12]2[C:8](=[CH:7][C:6]=1[O:14][C:15](=[O:17])[CH3:16])[CH2:9][CH2:10][CH2:11]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 20513349HCID 20513349, compound

Product 1

HCID 20513345HCID 20513345, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

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.

Sources & evidence

ORD record
ord-536399427da84808b9322a6f1a4fa80a
Source dataset
uspto-grants-1983_01
Patent number
US04367235

Reaction notes

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