Electric Literature of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A solution of 6 g (0.05 mol) of 4-aminophenol in a mixture of 50 mL of water and 15 mL of 32% hydrochloric acid was cooled on an ice bath to 0C. At continuous stirring maintaining the temperature below 5C a solution was added of 4 g (0.055 mol) of sodium nitrite in 15 mL of water. The obtained solution of a diazonium salt was stirred for 40 min. It was then added to a cooled to -5C solution of tin(II) chloride obtained by dissolving 30 g of tin in a mixture of 50 mL of water and 100 mL of 32% hydrochloric acid. After stirring for 2 h to the reaction mixture was added a solution of 0.05 mol of an appropriate isatin in a sufficient amount of 2-propanol, also a solution was added of 6 g (0.07 mol) of sodium acetate in 35 mL of water. The mixture obtained was stirred for 2 h, heated to 50C, and left standing for crystallization. The separated precipitate was filtered off and several times washed with water on the filter. The filtrate was additionally diluted with water, the separated precipitate was filtered off, washed with water on the filter, the precipitates were combined and dried.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.
Reference:
Article; Murashevich; Nichik; Zamyatina; Toropin; Burmistrov; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 650 – 654; Zh. Org. Khim.; vol. 52; 5; (2016); p. 665 – 669;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem