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With aluminum (III) chloride; In chlorobenzene; at 125℃; for 2h;
(b) 8-Bromo-2(1H)-quinolinone To a suspension of (2E)-N-(2-bromophenyl)-3-phenyl-2-propenamide (22.9 g, 76.0 mol) in chlorobenzene (100 ml) under an argon atmosphere at room temperature was added aluminium trichloride (60.78 g, 133.34 mmol). The reaction was heated for 2 hours at 125 C. after which time the reaction mixture was cooled to 50 C. before being carefully added to ice water (3 L). The resultant solid was filtered and then washed with water (500 ml), then triturated with hot ethanol, filtered and dried in vacuo to provide the desired compound as a white solid (7.39 g, 75%). MS (ES+) m/z 225 (MH+, 100%).
75%
To a suspension of (2£)-λ/-(2-bromophenyl)-3-phenyl-2-propenamide (22.9 g,76.0 mol) in chlorobenzene (100 ml) under an argon atmosphere at room temperature was added aluminium trichloride (60.78 g, 133.34 mmol). The reaction was heated for 2 hours at 125C after which time the reaction mixture was cooled to 500C before being carefully added to ice water (3 L). The resultant solid was filtered and then washed with water (500 <n="49"/>ml), then triturated with hot ethanol, filtered and dried in vacuo to provide the desired compound as a white solid (7.39 g, 75%). MS (ES+) m/z 225 (MH+, 100%).
57%
With aluminum (III) chloride; In chlorobenzene; at 120℃; for 0.5h;
Example 16 Intermediate 8-bromoquinolin-2(1H)-one To a solution of N-(2-bromophenyl)cinnamamide (67.18 mmol) in chlorobenzene (75 mL), aluminum chloride (335.90 mmol) was added incrementally. The mixture was brought to 120 C. then stirred for 30 minutes. The reaction solution was cooled to 50 C., poured over ice water (200 mL) and the solid was collected via vacuum filtration. The filtrate was placed in the refrigerator and a second crop of crystals was collected. Product residue was triturated with ethanol (100 mL) for 20 minutes then collected via vacuum filtration and placed under vacuum overnight. Yield: 8.62 g (57%).
Step 2B: Preparation- of 8-bromoquinolin-2(TH>one:; A mixture of N-(2- bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 1000C for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65 % yield) MS ESI (+) m/z 224 and 226 (M+l of each isotope) detected.
65%
A mixture of N-(2- bromophenyl)cinnamamide (172.3 g, 570.3 mmol), aluminum chloride (456 g, 342 mmol) and chlorobenzene (1000 ml) were allowed to stir at 1000C for 7 hours followed by cooling to ambient temperature overnight. The resulting mixture was poured onto 2 kg of ice and was allowed to warm to ambient temperature over 1 hour. The resulting mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting solids were triturated with 1000 ml hexanes. The solids were vacuum dried to yield title compound. (83 g, 65 % yield) MS ESI (+) m/z 224 and 226 (M+l of each isotope) detected.
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