These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-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. name: 5-(Trifluoromethoxy)indoline-2,3-dione
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-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5c): Melting point 255-257 C White solid, 97%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.98 (d, J = 3.96 Hz, 1H), 4.56-4.62 (m, 1H), 4.22-4.29 (m, 1H), 3.74 (d, J = 13.2 Hz, 1H), 3.63 (d, J = 16.82 Hz, 1H), 3.37 (d, J = 15.4 Hz, 1H), 2.90 (d, J = 13.96 Hz, 1H), 2.72-2.78 (m, 1H), 2.53 (d, J = 13.92 Hz, 1H), 6.53-6.62 (m, 2H), 6.88-7.55 (m, 21H, Ar); 13C-NMR(CDCl3, 100 MHz): delta/ppm 39.7, 47.3, 52.8, 53.2, 61.4, 67.2, 70.8, 100.8, 110.0, 121.9, 122.4, 122.5, 123.8, 124.3, 126.4, 126.5, 128.5, 128.6, 129.1, 129.2, 130.7, 131.5, 131.7, 131.9, 133.2, 136.2, 136.3, 138.1, 138.4, 138.6, 140.2, 144.6, 179.6, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.89; H, 3.81; N, 4.75.
The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.
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