Synthetic Route of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.
Sodium hydride 60% in mineral oil (0.750 mg, 30.0 mmol) and dry THF (150 ml) were added to a two-necked round-bottomed flask. Isoindolin-1-one (5) (2.50 g, 18.8 mmol) was added to the suspension at 0 C under N2. The reaction mixture wasstirred for 30 min at 0 C, and then potassium bromomethyl trifluoroborate (3.00 g, 15.0 mmol) was added to the reaction mixture in one portion and stirred for 30 min at 0 C. The reaction mixture was warmed to room temperature and refluxed for 48 h. The reaction mixture was cooled to 0 C and quenched by KHF2 (3.0 M) in H2O (14 mL). The reaction mixture was stirred at room temperature for 2 h. The solvents were removed under vacuum, and residue was dissolved in ethyl acetate (100 mL) and filtered. The solid obtained was triturated with boiling acetone (3 x 50 mL) and the resulting white powder was washed with cold ether (3 x 20 mL) and dried to give the potassium N-methyltrifluoroborate isoindolin-1-one (6) as white solid (2.54 g, 65%): mp: 229-234 C; IR (KBr, neat): 3032, 2936, 2897, 2879, 1658, 1590, 1473, 1455, 1426, 1415, 1306, 1228, 1210, 1099, 1069, 1011, 996, 760, 726, 538 cm-1; 1H NMR (DMSO-d6, 400 MHz) delta = 7.59 (d, J = 8.0 Hz, 1H), 7.53-7.46 (m, 2H), 7.42-7.39 (m, 1H), 4.38 (s, 2H), 2.47 (s, 2H); 13C NMR (DMSO-d6, 100 MHz) delta = 169.9, 144.0, 131.5, 131.2, 127.5, 123.7, 122.7, 44.8; 11B NMR (DMSO-d6, 128.37 MHz) delta = 3.46 (br s); 19F NMR (DMSO-d6, 376.49 MHz): delta = 138.67. HRMS (ESI-TOF) m/z calcd. for C9H8BNOF3 (M-K) 214.0651; found 214.0661.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.
Reference:
Article; Nadaf, Rashid N.; Seapy, Dave G.; Synthetic Communications; vol. 44; 14; (2014); p. 2012 – 2020;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem