Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 solution of 4b (1.00 g, 3.63 mmol) and 7b (1.11 g, 5.45 mmol) in THF (35 mL) was added NH4OAc (2.80 g, 36.3 mmol) in MeOH (35 mL). The reaction mixture was stirred at reflux temperature for 2 h and concentrated. The residue was diluted in CHCl3 and washed with a saturated aqueous solution of Na2CO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-5% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow amorphous (1.14 g, 69%): 1H NMR (200 MHz, CDCl3, delta): 2.42 (d, J = 0.7 Hz, 3H), 3.22 (t, J = 6.8 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 6.00 (s, 2H), 6.69 (s, 1H), 6.85 (d, J = 8.1 Hz, 1H), 7.09 – 7.35 (m, 2H), 7.69 – 7.87 (m, 4 H); MS (ESI) m/z 459 [M+H]+, 35%, 481 [M+Na]+, 100%, 457 [M-H]-, 100%. To a suspension of 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (1.12 g, 2.43 mmol) in EtOH (60 mL) was added hydrazine monohydrate (1.18 mL, 24.3 mmol). The reaction mixture was stirred at reflux temperature for 8 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by column chromatography on NH-silica gel eluting with 2-7% MeOH/CHCl3 to afford 8b as a pale yellow amorphous (567 mg, 71%): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.9 Hz, 3 H), 2.91 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9 Hz, 2 H), 6.00 (s, 2 H), 6.70 (d, J = 0.9 Hz, 1 H), 6.86 (d, J = 8.1 Hz, 1 H), 7.24 (dd J = 8.1, 1.7 Hz, 1 H), 7.36 (d, J = 1.7 Hz, 1 H); MS (ESI) m/z 329 [M+H]+, 90%, 351 [M+Na]+, 100%, 327 [M-H]-, 100%.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.
Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem