62541-59-7

Basic information

• Product Name: 7-NITRO-3,4-DIHYDROISOQUINOLINE
• Synonyms: 7-NITRO-3,4-DIHYDROISOQUINOLINE;7-Nitro-3,4-dihydroisoquinoline ,97%;3,4-dihydro-7-nitroIsoquinoline
• CAS NO: 62541-59-7
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Mol File: 62541-59-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-NITRO-3,4-DIHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-NITRO-3,4-DIHYDROISOQUINOLINE(62541-59-7)
• EPA Substance Registry System: 7-NITRO-3,4-DIHYDROISOQUINOLINE(62541-59-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 62541-59-7(Hazardous Substances Data)

Usage

Chemical Properties

Brick red powder

Upstream product

• 98590-39-7 2-(2-bromo-ethyl)-5-nitro-benzaldehyde 
• 198973-60-3 N-chlorotetrahydroisoquinoline 
• 42923-79-5 7-nitro-1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 3230-65-7 3,4-dihydroisoquinoline 

Downstream Products

• 13058-73-6 7-nitroisoquinoline 
• 62541-60-0 7-amino-3,4-dihydroisoquinoline 
• 174903-75-4 1-[1-(3,4-Dimethoxy-phenyl)-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone 
• 23707-37-1 7-aminoisoquinoline 
• 875002-69-0 N-(4-isopropyl-3-methylphenyl)-2-(isoquinolin-7-ylamino)nicotinamide 
• 1425782-76-8 N-(4-isopropyl-3-methylphenyl)-2-(isoquinolin-7-ylamino)nicotinamide 

Relevant articles and documents

Chemo-Enzymatic One-Pot Two-Step Functionalization of 1,2,3,4-Tetrahydroisoquinolines by Monoamine Oxidase-Ugi-Joullié Reaction Sequence

A one-pot two-step chemo-enzymatic approach for the functionalization of substituted 1,2,3,4-tetrahydroisoquinolines (THIQs) was developed. The system combines monoamine oxidase (MAO)-catalyzed imine formation with Ugi-type three-component reaction in an aqueous buffer without intermediate isolation. The two steps were separately optimized for buffer and pH to obtain the expected products. MAOs enabled the functionalization of fifteen THIQs by oxidation to imines, while the Ugi-Joullié-reaction was successfully carried out with eight carboxylic acids and eight isonitriles. 41 products were isolated giving access to valuable building blocks for medicinal chemistry applications. Gram-scale transformation demonstrated the utility of the described protocol for organic synthesis.

Construction of key building blocks towards the synthesis of cortistatins

This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. Cortistatin A, being a primary target due to its superior biological properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from d-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A.

Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode

Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).

Development of a scalable synthesis of a VEGFR inhibitor

Process development and salt selection for a novel VEGFR inhibitor are described. The overall convergent synthesis involved coupling of three key fragments, 2-chloronicotinoyl chloride, 4-isopropyl-3-methylaniline and 7-aminoisoquinoline. A cost-effective

Scalable synthesis of cortistatin A and related structures

Full details are provided for an improved synthesis of cortistatin A and related structures as well as the underlying logic and evolution of strategy. The highly functionalized cortistatin A-ring embedded with a key heteroadamantane was synthesized by a simple and scalable five-step sequence. A chemoselective, tandem geminal dihalogenation of an unactivated methyl group, a reductive fragmentation/trapping/elimination of a bromocyclopropane, and a facile chemoselective etherification reaction afforded the cortistatin A core, dubbed "cortistatinone". A selective δ16-alkene reduction with Raney Ni provided cortistatin A. With this scalable and practical route, copious quantities of cortistatinone, δ16-cortistatin A (the equipotent direct precursor to cortistatin A), and its related analogues were prepared for further biological studies.

Design of a highly efficient catalyst for the oxaziridinium-mediated epoxidation of olefins by Oxone

2,3,3-Trimethyl-7-nitro-3,4-dihydroisoquinolinium tetrafluoroborate is a highly efficient catalyst for the oxaziridinium-mediated epoxidation of a variety of olefins, including monosubstituted ones.

Preparation of 1,7-disubstituted-1,2,3,4-Tetrahydroisoquinolines

A simple procedure for the preparation of 1,7-disubstituted- 1,2,3,4-tetrahydroisoquinolines from 3,4-dihydroisoquinoline (2) is presented. This strategy overcomes the limitation of cyclisation approaches which generally require electron rich ring systems

A novel synthesis of isoquinolines containing an electron withdrawing substituent

3,4-Dihydroisoquinolines (10, 13) and isoquinolines (11), having various electron withdrawing substituent were synthesized in two steps from N- benzenesulfonyl- or N, N-dimethylsulfamoyl-β-phenethylamines (2 and 5). A novel cyclization method using ethyl chloro(methylthio)acetate (1) in the presence of SnCl4 as Lewis acid, followed by acid or base treatment provides the title compounds in good yield.

Synthesis of 1-aryl-2-acyltetrahydroisoquinolines with an electron withdrawing group in the aromatic ring of heterocycle

The intermolecular α-amidoalkylation reaction of adducts 3 obtained from acyl chlorides and 3,4-dihydroisoquinoline with an electron withdrawing group in the aromatic ring such as 7-nitro-3,4-dihydroisoquinoline towards aromatics has been investigated.