42792-95-0

Basic information

• Product Name: 2-methyl-5-nitroisoquinolinium
• CAS NO: 42792-95-0
• Molecular Formula: C₁₀H₉N₂O₂*I
• Molecular Weight: 189.1901
• Mol File: 42792-95-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-methyl-5-nitroisoquinolinium(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5-nitroisoquinolinium(42792-95-0)
• EPA Substance Registry System: 2-methyl-5-nitroisoquinolinium(42792-95-0)

Safety Data

• Hazardous Substances Data: 42792-95-0(Hazardous Substances Data)

Upstream product

• 607-32-9 5-nitroisoquinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 69337-15-1 1,2-dihydro-2-methyl-5-nitroisoquinoline 
• 42792-96-1 2-methyl-5-nitro-1(2H)-isoquinolinone 
• 948-43-6 N-methylacridinium iodide 
• 5412-06-6 N-methyl phenanthridinium iodide 
• 118629-89-3 2-methyl-3(R*)-ethoxy-5-nitro-9(S*)-(phenylthio)-1(S*),4(R*)-ethano-1,2,3,4-tetrahydroisoquinoline 
• 1074-86-8 4-formyl indole 
• 1074-85-7 (1H-indol-4-yl)methanol 
• 69062-53-9 Benzyl-(1H-indol-4-ylmethyl)-methyl-amine 

Relevant articles and documents

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Reactions of isoquinolinium salts with hydroxylamine derivatives, 2nd communication N-(alkyl) and N-(aryl) substituted compounds

The N-alkyl- and N-aryl-isoquinolinium salts 7, 15-17 reacted with free hydroxylamine in pyridine to give the isoquinoline-2-oxide (9) as final product. The intermediate dioximes 8 were isolated and characterized by derivatisation with acetic anhydride to the oxime ester nitrile 10. From the reaction of 8 with trifluoroacetic anhydride/triethylamine 3-amino-isoquinoline-2-oxide (12) resulted after hydrolysis. Due to the electronic influence the 5-nitroisoquinolinium salts 1-3 react faster than the 5-hydroxy derivative 20, but with the same course of conversion via dioximes to amine oxides. An optimized method for preparation of the amine oxides was developed.

A RATE AND EQUILIBRIUM STUDY OF THE ADDITION OF ACETONE ENOLATE ION TO THE 2-METHYL-5-NITROISOQUINOLINIUM CATION IN AQUEOUS SOLUTION

Rate and equilibrium constants for the reaction between acetone and the 2-methyl-5-nitroisoquinolinium cation to give 1-acetonyl-1,2-dihydro-2-methyl-5-nitroisoquinoline (2) have been evaluated over the pH range 10.0-11.3 in aqueous solutions at 25 deg C.This reaction is shown to occur under much milder conditions (temperature, pH) and in much shorter reaction times than previously used for the synthesis of this adduct.Analogous data for the reaction of hexadeuteroacetone with this heterocyclic cation are also presented.The formation of 2 is shown to be first order in each of acetone, isoquinolinium cation, and hydroxide ion, and is not catalyzed by carbonate buffer species.These data are consistent with the rate-determining attack of the acetone enolate anion upon the isoquinolinium cation.The microscopic reverse of this reaction is the uncatalyzed decomposition of 2, which is consistent with the observed pH independence of the first-order rate constant for this process.Quantitative comparisons of rates and equilibria for the addition of hydroxide ion and acetone enolate ion to this isoquinolinium cation and to substituted benzaldehydes are now available.