Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.
Stage 1: 5-nitro-isoindoline (I-12) A solution of isoindoline (3.9 g, 32.8 mmol, 1.0 eq.) in dichloromethane (20 mL) was stirred below -20 C. with exclusion of moisture while adding dropwise sulphuric acid (98%, 16.0 mL). The 2-layer mixture was allowed to reach 20 C. and then dichloromethane was removed under vacuum. The resulting pale brown solution was stirred and kept below 20 C. while adding nitric acid (70%, 3.9 mL) dropwise. The resulting pale orange-red solution was added with stirring to ice/water (300 mL) and tert-butyl methyl ether (100 mL). Sodium hydrogen carbonate (59 g) was added in portions and finally 4M aqueous sodium hydroxide (10 mL). The layers were separated and the aqueous phase extracted with tert-butyl methyl ether (4*150 mL). The combined organic phases were dried (sodium sulphate) and evaporated giving a red-brown gum (4.6 g, 85%) which was used in the next stage without purification. 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 8.05-8.19 (m, 2H) 7.38 (d, J=8.83 Hz, 1H) 4.32 (s, 4H) 2.14 (br. s., 1H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindoline, its application will become more common.
Reference:
Patent; INTERMUNE, INC.; US2010/119479; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem