Sep 2021 News Properties and Exciting Facts About Cinnolin-4-ol

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Example 20: Synthesis of 1- [4- (5-FLUORO-2-METHOXYPHENYL)-2-HYDROXY-4-METHYL-2- TRIFLUOROMETHYLPENTYL]-LH-CINNOLIN-4-ONE To a suspension of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et AL., Tetrahedron, 2000,56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 ML) was added sodium ethoxide (21 wt. % solution in ethanol, 276 PL). After heating at 85C for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m. p. 122C-123C.

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Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

14 Sep 2021 News Archives for Chemistry Experiments of 3-Bromocinnoline

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a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of 3-bromocinnoline, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%

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Reference:
Patent; Sanofi; US5147878; (1992); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

14 Sep 2021 News Downstream Synthetic Route Of 4-Aminocinnoline-3-carboxamide

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To a suspension of 4-aminocinnoline-3-carboxamide (3.5 g, 18.60 mmol) in DCM (10 ml) was added POCI3 (43.3 ml, 465 mmol) followed by triethylamine (7.78 ml, 55.8 mmol). The mixture was refluxed for 7 h. The reaction was then allowed to cool to 11 and conc, in vacuo. The crude residuewas then carefully treated with saturated aqueous NaHCO3 at 0 C. A precipitate formed which was collected via vacuum filtration. The filter cake washed with water (-i00 ml,), collected, and driedvacuo to provide the title compound as a grey solid 4-aminocinnoiine-3-carbonitriie.

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Reference:
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

14 Sep 2021 News The origin of a common compound about Methyl cinnoline-6-carboxylate

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Having gained chemical understanding at molecular level, chemistry graduates may choose to apply this knowledge in almost unlimited ways, as it can be used to analyze all matter and therefore our entire environment. 318276-74-3. Introduce a common compound, CAS is 318276-74-3, Name is Methyl cinnoline-6-carboxylate, belongs to cinnolinecompound.

A solution of the compound from example 3d) (345 mg; 1.8 mmol.) in anhydrous tetrahydrofuran (20.0 ml_) was cooled to 5 oC for the portionwise addition of solid lithium aluminumhydride (70.0 mg; 1.8 mmol.) and stirred at 5 0C for 1 h. The mixture was quenched by the addition of ethyl acetate (50.0 ml_) then water (5.0 ml_), filtered through a pad of Celite and evaporated. The residue was dissolved in ethyl acetate (50.0 ml.) and treated with manganese dioxide (0.50 g) and stirred at room temperature for 2 h. The mixture was filtered through a pad of Celite and evaporated to afford the title compound (169 mg; 60%) as a brown powder which was used directly in the following step without further purification, 318276-74-3

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Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/103759; (2007); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Sep 2021 News Downstream Synthetic Route Of Cinnoline-4-carboxylic acid

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EXAMPLE 2 Potassium Cinnoline-4-carboxylate (2) 5.10 g of (1) was added over 30 minutes to a vigorously stirred solution of 2.02 g of potassium carbonate in 25 ml of water, at room temperature. The resulting mixture was stirred for one hour at room temperature, then treated with charcoal, and after filtration the water was evaporated. The residue was azeotropically distilled with toluene and dried at 70 C. under reduced pressure, to give 2, as a light tan powder, m.p.: above 280 C.

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Reference:
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics