Application of 5181-35-1,Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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.
To a mixture of 2-(2-bromoetho xy)isoindo line- 1,3- dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 10) and 2H-tetrazole-5-carboxylic acid ethyl ester (10.51 g, 74 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at room temperature. After 16 hours, the reaction mixture was filtered through filter paper and filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the product was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layers were washed with brine (100 ml). The organic extract was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 12.5 g of the titled compound. The compound was purified by column chromatography using mixture of acetone and hexane as an eluent. The fractions containing the compound were collected and concentrated to provide 10 g of mixture of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}-2H-tetrazole-5-carboxylate in 53% yield Analysis: Mass: 332(M+1); for Molecular weight: 331 and for Molecular formula: C14H13N5O5 ; To a solution of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-2H-tetrazole-5-carboxylate (10 g, 3.02 mmol, product from step 1) in dichloromethane (100 ml) was added hydrazine hydrate (2.26 ml, 4.53 mmol) at 25- 30 C under stirring. The stirring was continued for 2 hours and the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent. After complete conversion of starting material, the unwanted solid was filtered out and washed with dichloromethane (20 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 6.0 g of mixture of ethyl l-[2-(aminooxy)ethyl]- lH-tetrazole-5-carboxylate and ethyl 2- [2-(aminooxy)ethyl]-2H-tetrazole-5-carboxylate (about 100% yield), the resulted compound was used in the next step without further purification.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Bromoethoxy)isoindoline-1,3-dione, its application will become more common.
Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem