Electric Literature of 3891-07-4, These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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.
Preparation of Ethyl 4-[2-(PHTHALIMIDO) ETHOXY] ACEFOACETATE (X1 A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 75 mL of tetrahydrofuran under nitrogen atmosphere. 7.53 g Sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 20 g of N- (2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 16.35 g ethyl 4-chloroacetoacetate in 30 ML of TETRAHYDRAFURAN was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 10 mL ethanol. The mixture was then poured into 150 mL of IN hydrochloric acid solution in crushed ice and 200 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of 5 wt. % OF NAHC03 solution, then with 150 ML of water, dried over 5 G of MgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 15 mL of hexane to remove the mineral oil to give 17.2 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate light brown product. (yield 51%, rel. compound purity > 80%). IR (KBR, CM~L) : 2995 and 1716. 1H-NMR (CDC13) 6 7.76 (dd, 2H), 7.65 (dd, 2H), 4.11 (S, 2H), 4.02 (q, 2H), 3.80 (t, 2H), 3.70 (t, 2H), 3.37 (s, 2H), 1. 16 (t, 3H). 13C-NMR (CDC13) 8 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 61.6, 46.0, 37.4, 14.3.
The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem