Electric Literature of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, its 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.
(iii) Preparation of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one : Charge 1.0 litre demin water, 100 gm of step (ii) product, 122.4 gm 3-(1-piperazinyl)-1,2-benzisothiazole HCl] and 138.2 gm of sodium carbonate into a 3 litre three neck flask at 25 to 30C. Stir for 15 mins and heat to reflux temperature 95 to 100C. Maintain at reflux temperature for 15 hrs. Cool the reaction mixture to 45-50C. Add 1.0 lt of demin water into the reaction mixture and stir for 30 mins. Filter at 45 to 50C and wash with demin water. Suck dry for 30 mins to yield crude product. Charge 2 lt of demin water and above crude product and heat the mixture gradually to 45 to 50C and stir for 30 mins. Filter the product at 45 to 50C and wash with demin water. Suck dry the product for 30 mins. Charge 2.0 lt of demin water and 300 gm of crude product into a 1.0 litre three neck flask at 25 to 30C and heat the mixture gradually to 45 to 50C. Stir for 30 mins. Filter the product at 45 to 50C and wash with demin water till about neutral pH (6.5 to 7.0). Suck dry the product for 30 mins to get wet crude base [5-[2- [4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one. Add 300 gms of wet crude base and 1.0 lt of isopropanol at 25 to 30C. Warm the reaction mixture to 50 to [55C] and stir for 1.0 hr. Cool the reaction mixture gradually to 10 to 15C and stir for 30 mins. Filter the product and wash with chilled isopropanol. Suck dry for 30 mins. Charge 300 gm of wet crude base and 6 lt of tetrahydrofuran (THF). Heat the reaction mixture gradually to reflux temperature 65- 70C. Reflux till clear solution. Cool to 50 to 55C and add charcoal and stir for 30 min at 50 to 55C. Filter the charcoal and wash with hot THF. Distill out THF at 50 to 55C under vacuum till residual volume is 1 lt and cool the reaction mixture gradually to 5 to 10C and stir for 1 hr. Filter the product and wash with chilled THF. Suck dry the product for 30 mins. Dry the product at 60 to 65C.
Statistics shows that 6-Chloro-5-(2-chloroethyl)indolin-2-one is playing an increasingly important role. we look forward to future research findings about 118289-55-7.
Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2003/99198; (2003); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem