75949-14-3

Basic information

• Product Name: 2(3H)-Isoquinolinamine, 3-imino-, mono(4-methylbenzenesulfonate)
• CAS NO: 75949-14-3
• Molecular Formula: C9H9N3.C7H8O3S
• Molecular Weight: 331.395
• Mol File: 75949-14-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2(3H)-Isoquinolinamine, 3-imino-, mono(4-methylbenzenesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Isoquinolinamine, 3-imino-, mono(4-methylbenzenesulfonate)(75949-14-3)
• EPA Substance Registry System: 2(3H)-Isoquinolinamine, 3-imino-, mono(4-methylbenzenesulfonate)(75949-14-3)

Safety Data

• Hazardous Substances Data: 75949-14-3(Hazardous Substances Data)

Upstream product

• 25475-67-6 isoquinolin-3-amine 
• 52913-14-1 O-tosylhydroxylamine 

Downstream Products

• 1006056-02-5 2-p-tolyl-[1,2,4]triazolo[1,5-b]isoquinoline 
• 1006056-08-1 (E)-3-(2-(4-methylbenzylidene)hydrazinyl)isoquinoline 
• 1006056-03-6 2-phenyl-[1,2,4]triazolo[1,5-b]isoquinoline 
• 1006056-10-5 (E)-3-(2-benzylidenehydrazinyl)isoquinoline 

Relevant articles and documents

A new synthesis of the linearly fused [1,2,4]triazolo[1,5-b]isoquinoline ring. Observation of an unexpected Dimroth rearrangement

A new and general synthesis of the linearly fused [1,2,4]triazolo[1,5-b]isoquinoline ring system starting from 2,3-diaminoisoquinolinium salts has been elaborated. Starting compounds bearing an alkyl group in position 4 easily reacted with aldehydes to yield the cyclized products. In the case of a lack of electron donating group in position 4 (e.g., unsubstituted or 4-cyano substituted diamino derivatives) a Dimroth rearrangement took place under the same reaction conditions to yield 3-isoquinolylhydrazones. The mechanism of this unexpected transformation has been verified by isotope labelling experiments. Clarification of the reaction mechanism allowed finding proper reaction conditions to eliminate the rearrangement route, and thus, to perfect successful ring closure to the fused triazoles.