34846-65-6

Usage

Uses

Used in Organic Synthesis:
Isoquinoline-4-carbonitrile is used as a precursor in the synthesis of various organic compounds. Its presence of a cyanide group allows for a range of chemical reactions, making it a versatile building block in the creation of complex molecules.
Used in Drug Discovery:
Isoquinoline-4-carbonitrile is utilized as an intermediate in the development of new pharmaceuticals. Its unique structure and reactivity contribute to the design and synthesis of potential drug candidates, particularly in the context of medicinal chemistry.
Used in Chemical Research:
Isoquinoline-4-carbonitrile is employed as a model compound in academic and industrial research settings. Its properties and reactivity are studied to gain insights into the behavior of similar compounds and to develop new synthetic methodologies and reaction pathways.
Used in Pharmaceutical Industry:
Isoquinoline-4-carbonitrile is used as a key intermediate in the production of certain pharmaceuticals. Its role in the synthesis of drug molecules highlights its importance in the development of new therapeutic agents and the improvement of existing medications.

InChI:InChI=1/C10H6N2/c11-5-9-7-12-6-8-3-1-2-4-10(8)9/h1-4,6-7H

Upstream product

• 1532-91-8 4-chloroisoquinoline 
• 557-21-1 dicyanozinc 
• 100-52-7 benzaldehyde 
• 117908-22-2 2-benzoyl-1,2-dihydro-1,4-isoquinolinedicarbonitrile 

Downstream Products

• 58123-56-1 isoquinolin-4-ylmethanamine 
• 7159-36-6 4-isoquinolinecarboxylic acid 
• 117908-22-2 2-benzoyl-1,2-dihydro-1,4-isoquinolinedicarbonitrile 
• 126225-73-8 2-(2-Bromo-benzyl)-4-cyano-isoquinolinium; bromide 
• 53000-96-7 1-oxo-2H-isoquinoline-4-carbonitrile 
• 20317-40-2 methyl isoquinoline-4-carboxylate 
• 116140-19-3 1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid 
• 126261-83-4 2-(2-bromobenzyl)-4-cyano-1,2-dihydroisoquinoline 

Relevant academic research and scientific papers

A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides

We report an efficient method for the preparation of aryl nitriles from aryl chlorides under either microwave assisted or thermal conditions. A catalyst system comprising tris(dibenzylidene acetone)dipalladium (Pd2(dba)3) and 2-(2′,6′-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) is shown to effectively promote cyanation of various aryl chlorides with Zn(CN)2 as the cyanide source.

Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles

Acid hydrolysis of 3-benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (11, 2-methylquinazoline Reissert compound) resulted in the formation of the oxazole (13).Alkaline hydrolysis gave 2-methylquinazoline (12) and banzoic acid (8).The anion (D1), generated from 11 and NaH in dimethylformamide (DMF), underwent decomposition to give the ketone (14) and the cyanoquinazoline (15) together with by-products 12 and O-benzoylbenzoin (9).Compound 11 reacted with aromatic aldehydes (10a-c) in the presence of NaH to give the benzoates (16a-c) and by-products 12 and 15.Alkylation (or arylation) with alkyl (or aryl) halides (11a, b) afforded the corresponding 4-substituted derivatives (19a, b) and a by-product 14.The reactivities of 11 and 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile (21, quinazoline Reissert compound) are compared. Keywords---Reissert compound; quinazoline; hydrolysis; Reissert compound anion; rearrengement; aromatization; electronic effect; electrophilic substitution