6-хлорникотиновую кисло

Химические свойства

Off-white to beige crystalline powder

Использование

6-Chloronicotinic acid is used as building block for different chemical synthesis. It is an intermediate for the synthesis of N-(thiophen-2-yl) benzamide derivatives as BRAFV600E inhibitors, and novel DNA-gyrase B inhibitors.

Определение

ChEBI: 6-Chloronicotinic acid is a member of pyridines and an aromatic carboxylic acid.

Общее описание

6-Chloropyridine-3-carboxylic acid is a metabolite of the neonicotinoid pesticides, imidacloprid and acetamiprid and occurs in different environmental matrices.(3) It is widely used in agricultural crop protection, domestic insect control and environmental pest management.

Синтез

In a 1000ml flask, add 450g chlorobenzene, 100g 2-chloro-5-methylpyridine, and 3g catalyst cobalt acetate under stirring, heat the system to 80℃, introduce oxygen, and control the oxygen flow rate at 0.4L/min. React under this condition for 4 hours. After the reaction, cool the system to room temperature, filter, and dry to obtain a mixture of 119g 6-chloronicotinic acid and cobalt acetate. Place those mentioned above mixed crude product in a 1000ml flask, add 600g of recrystallization solvent methanol, stir and heat to reflux; wait for the 6-chloronicotinic acid crude product to dissolve completely, keep warm for 5min, slowly cool the system to 5℃, precipitate a white product, maintain this internal temperature and continue stirring for 1 hour, filter, wash the filter cake once with a small amount of cooled methanol, and dry the obtained damp product at 80℃ for 4 hours to obtain 98.5g 6-chloronicotinic acid, purity 99.52% (HPLC), yield 79.7%.

Методы очистки

Purify it by recrystallisation from hot H2O and sublime it in a vacuum. [Pechmann & Welsch Chem Ber 17 2384 1884, Herz & Murty J Org Chem 26 122 1961, Beilstein 22/2 V 177.]