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a) 6-Bromo-2,3 -dihydro- 1 H-quinolin-4-one4-Bromoaniline (2.Og, 11.6 mmol) and acrylic acid (0.95 mL, 13.9 mmol) were stirred in toluene (15 mL) at 1000C for 3 days. After cooling, the reaction mixture was extracted with IN NaOH (150 mL). The aqueous layer was acidified with 2N HCl (pH~3) and subsequently extracted with ethylacetate (2x100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford N-(4-bromophenyl)-3- aminopropionic acid (1.65g, 58percent). A mixture of the carboxylic acid (1.64g, 6.72 mmol) in polyphosphoric acid (30g) was stirred at 9O0C overnight. The reaction was allowed to cool and ice-water was added. The mixture was then extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with IN NaOH, water and brine respectively. Drying (Na2SO4) and concentration afforded the cyclized product (0.88g, 58percent). 1H NMR (d-chloroform) δ (ppm): 2.67 (t, 2H), 3.54 (t, 2H), 6.57 (d, IH), 7.33 (dd, IH), 7.92 (s, IH).
3%
at 55℃;
Crude 3-((4-bromophenyl)amino)propanoic acid (4.1 mmol based on theoretical yield)was dissolved in Eaton’s reagent (12.3 g) at a ratio of 3 g Eaton’s reagent per mmol ofS41carboxylic acid. The solution was heated to 55 °C overnight. After cooling to roomtemperature, the reaction was quenched over ice. The product was extracted with ethyl acetate(3 × 25 mL), washed with brine, dried over Na2SO4. Purification using flash chromatography(silica gel, hexanes: ethyl acetate, 83:17 to 0:100) afforded pure 6-bromo-2,3-dihydroquinolin-4(1H)-one (0.029 g, 0.130 mmol, 3 percent yield).
Reference：
[1] Patent: WO2009/39553, 2009, A1, . Location in patent: Page/Page column 93
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2801 - 2807
a) 6-Bromo-2,3 -dihydro- 1 H-quinolin-4-one4-Bromoaniline (2.Og, 11.6 mmol) and acrylic acid (0.95 mL, 13.9 mmol) were stirred in toluene (15 mL) at 1000C for 3 days. After cooling, the reaction mixture was extracted with IN NaOH (150 mL). The aqueous layer was acidified with 2N HCl (pH~3) and subsequently extracted with ethylacetate (2x100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford N-(4-bromophenyl)-3- aminopropionic acid (1.65g, 58%). A mixture of the carboxylic acid (1.64g, 6.72 mmol) in polyphosphoric acid (30g) was stirred at 9O0C overnight. The reaction was allowed to cool and ice-water was added. The mixture was then extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with IN NaOH, water and brine respectively. Drying (Na2SO4) and concentration afforded the cyclized product (0.88g, 58%). 1H NMR (d-chloroform) delta (ppm): 2.67 (t, 2H), 3.54 (t, 2H), 6.57 (d, IH), 7.33 (dd, IH), 7.92 (s, IH).
With acetic acid; In water; for 18.0h;Reflux;
4-Bromoaniline (0.500 g, 2.91 mmol), acrylic acid (0.199 mL, 2.91 mmol), and 20 %acetic acid (2 mL) were combined in a round bottom flask. The reaction mixture was heated toreflux with stirring for 18 h. The crude product was obtained as a brown oil at this point andtaken on to cyclization without purification.
a) 6-Bromo-2,3 -dihydro- 1 H-quinolin-4-one4-Bromoaniline (2.Og, 11.6 mmol) and acrylic acid (0.95 mL, 13.9 mmol) were stirred in toluene (15 mL) at 1000C for 3 days. After cooling, the reaction mixture was extracted with IN NaOH (150 mL). The aqueous layer was acidified with 2N HCl (pH~3) and subsequently extracted with ethylacetate (2x100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford N-(4-bromophenyl)-3- aminopropionic acid (1.65g, 58%). A mixture of the carboxylic acid (1.64g, 6.72 mmol) in polyphosphoric acid (30g) was stirred at 9O0C overnight. The reaction was allowed to cool and ice-water was added. The mixture was then extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with IN NaOH, water and brine respectively. Drying (Na2SO4) and concentration afforded the cyclized product (0.88g, 58%). 1H NMR (d-chloroform) delta (ppm): 2.67 (t, 2H), 3.54 (t, 2H), 6.57 (d, IH), 7.33 (dd, IH), 7.92 (s, IH).
3%
With Eaton?s reagent; at 55.0℃;
Crude <strong>[90561-83-4]3-((4-bromophenyl)amino)propanoic acid</strong> (4.1 mmol based on theoretical yield)was dissolved in Eaton?s reagent (12.3 g) at a ratio of 3 g Eaton?s reagent per mmol ofS41carboxylic acid. The solution was heated to 55 C overnight. After cooling to roomtemperature, the reaction was quenched over ice. The product was extracted with ethyl acetate(3 × 25 mL), washed with brine, dried over Na2SO4. Purification using flash chromatography(silica gel, hexanes: ethyl acetate, 83:17 to 0:100) afforded pure 6-bromo-2,3-dihydroquinolin-4(1H)-one (0.029 g, 0.130 mmol, 3 % yield).
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