Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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. name: 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid
To a solution of 3-(1,3-dioxoisoindolin-2-yl)propanoic acid (300 mg, 1.31 mmol) in dichloromethane (5mL) at r.t. was added thionyl chloride (0.15 mL, 2.06 mmol) and the mixture was heated at reflux for 2h. The mixture was then concentrated by rotary evaporator to afford 3- (1,3-dioxoisoindolin-2-yl)propanoyl chloride, which was used immediately for the next reaction. To asolution of 3-(1,3-dioxoisoindolin-2-yl)propanoyl chloride in dry dichloromethane (5 mL) was added phenothiazine (200 mg, 1 mmol) and pyridine (0.5 mL) at 0 C. After being stirred at r.t. for 5 h, the reaction was quenched by 3 mol¡ÁL-1 hydrochloric acid (10 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (2 ¡Á 15 mL). The combined organic extracts were washed with saturated NaHCO3, dried with Na2SO4 and rotary evaporated. The crude product was recrystallized from 95% ethanol to afford 6c (380 mg, 95.0%) as white soild, m.p. 256.5-257.5 C. 1H NMR (300 MHz, CDCl3): delta 8.48 (s, 1H), 7.81 (dd, J = 5.4, 3.0 Hz, 2H), 7.69 (dd, J = 5.4, 3.0 Hz, 2H), 7.49 (d, J = 6.6 Hz, 2H), 7.42 (d, J = 7.8 Hz, 2H), 7.31 (t, J = 7.2 Hz, 2H), 7.21 (t, J = 7.5 Hz, 2H). 13C NMR (100 MHz, CDCl3): delta 169.15, 168.03, 138.27, 134.01, 133.92, 132.10, 128.06, 127.11, 126.97, 123.25, 34.28, 32.74. ESI-HRMS m/z calcd. for C23H17N2O3S ([M+H]+) 401.0954, found 401.0960.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3339-73-9, its application will become more common.
Reference:
Article; He, Chun-Xian; Meng, Hui; Zhang, Xiang; Cui, Hua-Qing; Yin, Da-Li; Chinese Chemical Letters; vol. 26; 8; (2015); p. 951 – 954;,
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