36073-93-5

Usage

Uses

Used in Pharmaceutical Synthesis:
4-NITROISOQUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new and effective medications.
Used in Organic Chemistry:
As a reagent, 4-NITROISOQUINOLINE is utilized in organic chemistry to facilitate specific reactions and transformations, enhancing the synthesis of complex organic compounds.
Used in Drug Research and Development:
4-NITROISOQUINOLINE is employed as a building block in the research and development of new drugs, contributing to the discovery of innovative therapeutic agents.
Used in the Production of Fine Chemicals:
In the fine chemicals industry, 4-NITROISOQUINOLINE is used as a component in the production of high-quality specialty chemicals, which are essential for various applications, including pharmaceuticals, fragrances, and agrochemicals.

InChI:InChI=1/C9H6N2O2/c12-11(13)9-6-10-5-7-3-1-2-4-8(7)9/h1-6H

Upstream product

• 119-65-3 isoquinoline 
• 192182-56-2 4-isoquinolineboronic acid 

Downstream Products

• 111493-33-5 4,5-dinitroisoquinoline 
• 23687-25-4 4-aminoisoquinoline 
• 78886-54-1 1-Amino-4-nitroisoquinoline 
• 1432028-30-2 2-ethyl-4-nitroisoquinolinium tetrafluoroborate 
• 1432028-32-4 2-ethyl-4-nitro-1(2H)-isoquinolinium hydroperoxide 
• 1432028-34-6 2-ethyl-4-nitro-1(2H)-isoquinolinone 
• 111493-34-6 pyrido<3,4,5-de>quinazoline-2-thione 
• 110748-36-2 1H-pyrido<3,4,5-de>quinazoline 
• 110191-89-4 isoquinoline-4,5-diamine 
• 342899-40-5 N-(3-chloro-4-isoquinolinyl)-2-cyclopropylamino-3-pyridinecarboxamide 
• 342899-39-2 2-chloro-N-(3-chloro-4-isoquinolinyl)-3-pyridinecarboxamide 
• 342899-38-1 4-amino-3-chloroisoquinoline 

Relevant academic research and scientific papers

Catalyst-free ipso-nitration of aryl boronic acids using bismuth nitrate

We report a catalyst-free ipso-nitration of aryl boronic acids using bismuth (III) nitrate as nitrating agent. Reaction proceeds in shorter reaction times with moderate to excellent yields. This method is operationally simple, regioselective, and possesses excellent functional group compatibility to synthesize nitroarenes.

Preparation of nitropyridines by nitration of pyridines with nitric acid

Preparation of nitropyridines by nitration of pyridines with nitric acid was discussed. Trifluoroacetic anhydride was chilled in an ice bath and the pyridine or substituted pyridines were slowly added and stirred at chilled conditions for 2 h. Relative amounts of the reactants were required for the nitration of pyridine were characterized by 1H and Nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. It was observed that the yields of β-nitropyridines obtained using the standard protocol were generally higher than those obtained using N2O3.

Preparation of novel heteroisoindoles from nitropyridines and nitropyridones

The reaction of nitropyridine derivatives with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene proceeded tandem cyclization to give polycyclic pyrrolopyridines or imidazopyridines. On the other hand, N-protected 3-nitro- and 5-nitropyridones and N,N-diprotected 5-nitrouracil gave corresponding bicyclic pyrroles in good yields under the similar conditions.

The synthesis of β-nitropyridine compounds

Pyridine and a number of substituted pyridines have been nitrated by reaction with N2O5 followed by reaction with an aqueous solution of SO2xH2O or NaHSO3. The dependence of the yields on the pH of the aqueous reaction medium, on the concentration of SO2xH2O-HSO3-, on addition of methanol to the aqueous phase, and on the reaction temperature were investigated. The yields obtained with NaHSO3 were: 3-nitropyridine 77%, 2-methyl-5-nitro-pyridine 36%, 3-methyl-5-nitropyridinc 24%, 3-acetyl-5-nitropyridine 18%, 5-nitropyridine-3-carboxylic acid 15%, 3-chloro-5-nitropyridine 11%, 4-methyl-3-nitropyridine 39%, 4-acetyl-3-nitropyridine 67%, 4-cyano-3-nitropyridine 45%, 4-phenyl-3-nitropyridine 68%, 4-formyl-3-nitropyridine 62% (from reaction in liquid SO2), 3-nitropyridine-4-carboxylic acid 48%, methyl 3-nitropyridine-4-carboxylate 75%, 2,3-dimethyl-5-nitropyridine 37%, 2,4-dimethyl-5-nitropyridine 64%, 3-nitroquinoline 10% and 4-nitroisoquinoline 42%.

A new efficient synthesis of 3-nitropyridine and substituted derivatives

Pyridine and pyridine derivatives have been nitrated in the β-position by reaction with N2O5 or NO2·BF4 in MeNO2, THF or MeCN to form the N-nitropyridinium salt. This was then reacted with an aqueous solution of a nucleophile to give the β-nitro compound in moderate to good yield.