Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1074-82-4, Product Details of 1074-82-4
Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use. 1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.
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Reference:
Patent; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem