6-BroMo-4-phenylquinolin-2(1H)-one synthesis
- Product Name:6-BroMo-4-phenylquinolin-2(1H)-one
- CAS Number:178490-58-9
- Molecular formula:C15H10BrNO
- Molecular Weight:300.15
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Yield:178490-58-9 88%
Reaction Conditions:
Stage #1: 2-amino-5-bromobenzophenonewith lithium hexamethyldisilazane in tetrahydrofuran at 0; for 0.5 h;
Stage #2: ethyl acetate in tetrahydrofuran;water at 0 - 20; for 20 h;
Steps:
1.2 Step 2: Synthesis of 6-bromo-4-phenylquinolin-2(lH)-one
To a stirred solution of (2-amino-5-Bromophenyl) (phenyl)methanone (12 g, 0.0436 mmol) in THF (100 mL) at 0°C was added LiHMDS (260 mL, 0.261 mmol,lM in THF) and stirred for 0.5 h before the addition of ethyl acetate (12.79 mL). The reaction mixture was continued and stirred at 0°C for a period of 4 h. The reaction mixture was slowly warmed to room temperature and water (50 mL) was added to the reaction mixture. Resultant mass was stirred at RT for a period of 16h. After completion of the reaction (monitored by T.L.C, Eluent:30% EtOAc/Hexane, R.f: 0.3), hexane (200 mL) was added to the reaction mixture, and the precipitated solid was filtered, washed with water and dried under vacuum to afford 6-bromo-4-phenylquinolin-2(lH)-one (11.5 g, 88%) as an off white solid. MS (ESI) m/z: 399.0 [M + H] +.
References:
WO2021/150645,2021,A1 Location in patent:Page/Page column 212-214
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