Related Products of 5394-18-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5394-18-3 name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: Chemistry. Compounds 4-10 were synthesized following methodologies previously reported and the analytical and structural data was in agreement with formerly published data.1, 2 Briefly, 4,7-dichloroquinoline or 4-chloropyridine, respectively, was reacted at 100 ºC for 2 to 3 h with 10 molar equivalents (eq) of the respective diaminoalkane to afford the resultant amine; the reaction mixture was then brought to room temperature and diluted with dichlorometane (DCM), and the solution washed with 5% aqueous Na2CO3. The organic layer was isolated and dried over anhydrous Na2SO4, filtered, and the filtrate evaporated to dryness. In the case of the morpholine derivative, 2 eq of morpholine were reacted with 1 eq of 1-(N-phthaloyl)amino-4-bromobutane for 1 day to yield N-(N-phthaloyl)aminobutylmorpholine; after the previously described extraction process, the phthalimide group of the latter compound was removed with hydrazine in ethanol to afford the desired amine. Following, the respective cinnamic acid was activated in N,N-dimethylformamide (DMF), using 2 eq of O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate and 2 eq of N,N-diethyl-N-isopropylamine (DIEA) at 0 oC for 10 min. Subsequently, the corresponding amine was added and the mixture was left to react for 1 day. The mixture was then diluted in DCM, washed with 5% aqueous Na2CO3 and the organic layer collected, dried over Na2SO4, filtered, and the filtrate evaporated to dryness. The crude product was further purified by column liquid chromatography on silica, using a mixture of ethyl acetate and methanol (8:2 v/v) as eluent.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromobutyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.
Reference:
Article; Perez, Bianca C.; Fernandes, Iva; Mateus, Nuno; Teixeira, Catia; Gomes, Paula; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6769 – 6772;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem