Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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. SDS of cas: 169037-23-4
General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(p-chlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-chlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5f): Melting point 259-261 C; white solid, 95%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.60 (d, J = 13.92 Hz, 1H), 4.18-4.23 (m, 1H), 3.86 (d, J = 10.28 Hz, 1H), 3.24-3.38 (m, 2H), 2.92-3.00 (m, 2H), 2.50-2.54 (m, 1H), 2.33-2.39 (m, 1H), 6.53-6.56 (m, 2H), 6.67-7.02 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.8, 46.9, 52.3, 53.1, 61.5, 65.9, 70.7, 100.4, 109.8, 123.9, 124.1, 126.0, 128.1, 128.2, 128.4, 128.7, 128.8, 129.0, 130.4, 131.4, 132.5, 132.6, 135.8, 135.9, 136.4, 140.6, 143.7, 136.2, 137.6, 138.5, 139.9, 144.4, 179.1, 196.9. EI-MS: m/z 780 (M+). Anal. Calcd for C44H34Cl2F3N3O3: C, 67.70; H, 4.39; N, 5.38; Found: C, 67.59; H, 4.51; N, 5.25.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 169037-23-4, its application will become more common.
Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem