Electric Literature of 172078-33-0,Some common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, molecular formula is C8H9NO, 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 stirred solution of 6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-l-(pyri- din-2-ylmethyl)-l,2-dihydroquinoline-3-carbaldehyde (intermediate- le) (0.2 g, 0.51 mmol) in titanium isopropoxide (5 mL) was added indolin-5-ol (0.1 g, 0.77 mmol) followed by stirring at RT for 16 h. After stirring, methanol (20 mL) was added to the mixture at 0 C followed by NaCNBH4 (0.16 g, 2.56 mmol). The mixture was stirred at RT for 2 h. The mixture was then quenched with ammonium hydroxide and the solids were filtered off. The filtrate was extracted with EtOAc (100 mL x 2), washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified to get the title compound as pale brown solid (0.016 g, 6 %). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J=4.8 Hz, 1H), 7.86 (s, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.23-7.20 (m, 2H), 6.69 (s, 1H), 6.60-6.48 (m, 2H), 5.74 (s, 2H), 4.29 (s, 2H), 3.79 (s, 3H), 3.61-3.59 (m, 2H), 3.10-3.00 (m, 2H), 2.25 (s, 3H), 2.11 (s, 3H); LC-MS: m/z 509.3 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-5-ol, its application will become more common.
Reference:
Patent; ORION CORPORATION; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; LINNANEN, Tero; WOHLFAHRT, Gerd; (120 pag.)WO2017/1733; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem