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Usage

Uses

Used in Pharmaceutical Synthesis:
3-Amino-4-methylisoquinoline is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of novel drug molecules. Its unique structure allows for the creation of compounds with potential therapeutic effects.
Used in Dye Production:
In the dye industry, 3-Amino-4-methylisoquinoline is utilized as a precursor for the production of various dyes. Its chemical properties enable the creation of dyes with specific color characteristics and stability.
Used in Organic Synthesis:
3-Amino-4-methylisoquinoline serves as a versatile building block in organic synthesis, where it is used as a starting material for the preparation of a wide range of organic compounds. Its reactivity and structural features facilitate the synthesis of complex organic molecules.
Used in Medicinal Chemistry Research:
3-Amino-4-methylisoquinoline is employed as a subject of interest in medicinal chemistry research due to its potential biological activities. Researchers explore its interactions with biological targets to discover new therapeutic agents and understand its mechanisms of action.
Used in Drug Development:
Owing to its unique structure and properties, 3-Amino-4-methylisoquinoline is used in the development of new drugs. Its potential to be modified and combined with other chemical entities makes it a valuable component in the creation of innovative pharmaceuticals with improved efficacy and selectivity.

InChI:InChI=1/C10H10N2/c1-7-9-5-3-2-4-8(9)6-12-10(7)11/h2-6H,1H3,(H2,11,12)

Upstream product

• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 1491842-34-2 tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 28970-71-0 1-bromo-4-methyl-isoquinolin-3-ylamine 

Downstream Products

• 109000-49-9 C₁₆H₁₃ClN₄ 
• 109000-51-3 C₁₆H₁₃N₅O₂ 
• 109000-50-2 C₁₆H₁₃FN₄ 
• 109000-48-8 C₁₆H₁₃BrN₄ 
• 75949-19-8 2,3-diamino-4-methylisoquinolinium 4-methylbenzenesulfonate 
• 1370708-50-1 4-methyl-N-(4-nitrophenyl)isoquinolin-3-amine 
• 1370708-47-6 4-methyl-N-(2-nitrophenyl)isoquinolin-3-amine 
• 1400699-84-4 N-methoxy-4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}-sulfonyl)benzamide 
• 1400699-83-3 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}sulfonyl)-benzamide 

Relevant academic research and scientific papers

Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines

The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot isoquinoline synthesis. Alternatively, cyclization of the intermediates with hydroxylamine hydrochloride engenders direct access to isoquinoline N-oxides; and cyclization with methylamine, gives isoquinolinium salts. Significant diversity is available in the substituents at the C4 position in four-component, one-pot couplings, by either trapping the in situ intermediate after α-arylation with carbon or heteroatom-based electrophiles, or by performing an α,α-heterodiarylation to install aryl groups at this position. The α-arylation of nitrile and ester enolates gives access to 3-amino and 3-hydroxyisoquinolines and the α-arylation of tert-butyl cyanoacetate followed by electrophile trapping, decarboxylation and cyclization, C4-functionalized 3-aminoisoquinolines. An oxime directing group can be used to direct a C-H functionalization/bromination, which allows monofunctionalized rather than difunctionalized aryl precursors to be brought through this synthetic route.

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladiu

New fluorescent isoquinoline derivatives

Various structural modifications of 3-amino and 3-hydroxyisoquinolines have been carried out to provide new fluorescent derivatives. The transformations involved nucleophilic substitution of a bromine atom or a triflate moiety at positions 1 and 3, respectively, as well as the condensation reaction of a 3-amino group with triethyl orthoformate and subsequent transformation with amines to give amidines. The new compounds have been studied by fluorescence spectroscopy.