10590-69-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Cyano-4-methylquinoline is used as a chemical intermediate for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and pesticides.
Used in Dye and Pigment Production:
2-Cyano-4-methylquinoline is used as a key ingredient in the production of dyes and pigments. Its yellow color and crystalline nature contribute to the color intensity and stability of the final products.
Used in Organic Light-Emitting Diode (OLED) Manufacturing:
2-Cyano-4-methylquinoline is utilized in the manufacturing of organic light-emitting diodes (OLEDs). Its chemical properties make it suitable for use in the creation of efficient and long-lasting OLED devices.

InChI:InChI=1/C11H8N2/c1-8-6-9(7-12)13-11-5-3-2-4-10(8)11/h2-6H,1H3

Upstream product

• 4053-40-1 4-methylquinoline 1-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 557-21-1 zinc(II) cyanide 
• 634-47-9 2-chloro-4-methylquinoline 
• 33787-85-8 (4-methyl-quinolin-2-yl)-methanol 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 56947-80-9 2-cyclohexyl-4-methylquinoline 
• 62093-18-9 N,4-dimethyl-N-phenylquinoline-2-amine 

Relevant academic research and scientific papers

Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway

Quinolines and isoquinolines were treated with Na2S2O8 in a mixture of methanol and water at 70 °C to form hydroxymethylated quinolines and isoquinolines in good to moderate yields, under transition-metal-free conditions. The formed hydroxymethyl group was smoothly converted into aldehyde, ester, amide, bromomethyl, (N,N-diethylamino)methyl, cyano, and tetrazole groups, in good yields.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Synthesis method of 2-cyanoquinoline derivative

The invention discloses a synthesis method of a 2-cyanoquinoline derivative, and belongs to the technical field of synthesis methods of chinoline and derivatives thereof. The synthesis method includes: adopting a compound represented as in formula (I) and trimethylsilyl cyanide as raw materials, dissolving the raw materials in an organic solvent, catalyzing with H-diethyl phosphite and carbon tetrachloride, and adopting alkali as a deacid reagent to prepare a compound represented as in formula (II). The synthesis method of the 2-cyanoquinoline derivative has the advantages that the adopted catalysts are low in cost and easy to obtain, the raw materials are easy to store, reaction conditions are mild, experimental operations are simple, the obtained 2-cyanoquinoline derivative products are easy to purify, high yield and applicability to industrial production are realized, and a novel synthesis method for preparing the 2-cyanoquinoline derivative is provided.

Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide

A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).

Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound

The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.

Pd-Catalyzed Cyanation of (Hetero)Aryl Halides by Using Biphosphine Ligands

Tetraadamantylbiphosphine (TABP; L1), which showed superior activity in the palladium-catalyzed cyanation of 4-chloroanisole compared to standard phosphines, was synthesized as a new ligand. The generality of the new catalytic system was shown by the cyanation reaction of approximately 30 (hetero)aryl halides including hindered, electron-rich, and electron-poor aryl chlorides. These reactions constitute the first examples of using biphosphine ligands in Pd-catalyzed coupling reactions.

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

A Homogeneous Method for the Conveniently Scalable Palladium- and Nickel-Catalyzed Cyanation of Aryl Halides

Homogeneous conditions for the palladium-catalyzed cyanation of aryl halides were developed. This new system features a broad scope of aryl chlorides and bromides, uses 2-propanol or 1-butanol as solvent, and is readily scalable. The same conditions can also provide simple benzonitriles using the recently developed (TMEDA)NiCl(o-tolyl) precatalyst in conjunction with 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand.

Polycyclic N-heterocyclic compounds. Part 52. One-step syntheses of imidazo[1,5-a]pyridines, imidazo[1,5-a]quinolines and imidazo[5,1-a]isoquinolines by Vilsmeier reactions of pyridine-2-carbonitriles, quinoline-2-carbonitriles and isoquinoline-1-carbonitriles

The versatile, one-step synthesis of imidazo[1,5-a]pyridines by the reaction of pyridine-2-carbonitriles with DMF under Vilsmeier conditions is described. This reaction was applied to the syntheses of imidazo[1,5-a]quinolines from quinoline-2-carbonitriles, and of imidazo[5,1-a]isoquinolines from isoquinoline-1-carbonitriles.

An Improved Synthesis of Homoproline and Derivatives

An improved, general synthesis of substituted homoprolines has been developed by using readily available substituted pyridines (1).A key step in this synthetic procedure involves the known conversion of pyridine-N-oxides to 2-cyanopyridines (3) in nearly quantitative yields.The resulting nitriles are hydrolyzed to the corresponding pyridine-2-carboxylic acids (4).Subsequent reduction of the aromatic ring with PtO2/H2 gives the homoprolines (5) in good yields as racemic cis isomers.This procedure also can be utilized for the preparation of 5,6-benzohomoprolines fromthe appropriate quinoline precursors.The N-tert-butyloxycarbonyl (Boc) derivatives of these amino acids (useful intermediates for peptide synthesis) were also prepared in good yields.