22902-57-4

Basic information

• Product Name: 10-Nitrobenzimidazo[2,1-a]isochinolin
• CAS NO: 22902-57-4
• Molecular Weight: 263.255
• Mol File: 22902-57-4.mol

Chemical Properties

• CAS DataBase Reference: 10-Nitrobenzimidazo[2,1-a]isochinolin(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Nitrobenzimidazo[2,1-a]isochinolin(22902-57-4)
• EPA Substance Registry System: 10-Nitrobenzimidazo[2,1-a]isochinolin(22902-57-4)

Safety Data

• Hazardous Substances Data: 22902-57-4(Hazardous Substances Data)

Relevant articles and documents

Reactions of isoquinolinium salts with hydroxylamine derivatives, 3rd communication. Mechanism of amine oxide generation

2-Methylpapaverinium iodide (1) reacted with hydroxylamine to papaverine-N-oxide (2), but without a detectable intermediate and only in moderate yield, caused by the steric hindrance of the 1-substituent. The ring opened product of 2-dinitrophenylisoquinolinium salt with hydroxylamine, the enamine-oxime 3b gave rise to a 3-substituted cyclic nitrone (6), when heated with triethylamine. This alkali-stable compound was transformed with acid quantitatively to isoquinoline-N-oxide (4). The enaminonitrile 9c, treated with triethylamine showed cyclization to the iminoisoquinoline 10, which by loss of nitrous acid produced the tetracyclic azaindole 11. The 2-methoxyisoquinolinium salt 16 was cleaved with O-methylhydroxylamine to the resistant di(O-methyloximes) (20a/b), unable to form the amine oxide 4. From these and former results, a mechanism for the ring opening of cycliminium salts and the recyclization to amine oxides was proposed.