5-Acetyl-8-(phenylmethoxy)-2(1H)-quinolinone

White or off-white solid powder

Crude 5-ACETYL-8-HYDROXY-(1H)-QUINOLIN-2-ONE (8.13 g, 40 mmol, 1.0 eq. ) is added to N- N, diisopropylethylamine (6.46 g, 50 mmol, 1.25 eq. ) and acetone (64 mL). The suspension is heated to reflux temperature and water is added (8.2 mL). Benzylbromide (7.52 g, 44 mmol, 1.10 eq. ) is added drop-wise and the reaction is maintained for 6-7 hours at reflux temperature until all starting material has reacted. Water (20 mL) is added at IT = 58 °C and the mixture is cooled down to 20-25 °C. The product is filtered, washed with acetone/water (1/1, 2 x 8.5 mL) and then with water (4 x 8 mL). The crude product is dried overnight under vacuum (60 °C). Yield: 10.77 g (91.7percent). Purity of the crude product: 99.5percent. The product may be recrystallized from acetone/water. Preparation of 5-acetyl-8-benz, Ylo , -x(at)Il(at)duinolin-2-one; [Crude 5-acetyl-8-hydroxy-(lM-quinolin-2-one (8.13 g, 40 mmol, 1.0 eq.) is added to N- N, diisopropylethylamine (6.46 g, 50 mmol, 1.25 eq. ) and acetone (64 mL). The suspension is heated to reflux temperature and water is added (8.2 mL). Benzylbromide (7.52 g, 44 mmol, 1.10 eq. ) is added drop-wise and the reaction is maintained for 6-7 hours at reflux temperature until all starting material has reacted. Water (20 mL) is added at IT = 58 °C and the mixture is cooled down to 20-25 °C. The product is filtered, washed with acetone/water (1/1, 2 x 8.5 mL) and then with water (4 x 8 mL). The crude product is dried overnight under vacuum (60 °C) . Yield: 10.77 g (91.7percent). Purity of the crude product: 99.5percent. The product may be recrystallised from acetone/water.To a solution of 5-acetyl-8-hydroxy-(1H)-quinolin-2-one (35 g) in dimethylformamide (175 ml) potassium carbonate (35 g) was added at room temperature and stirred for 10 minutes. To the suspension, benzylbromide (32 g) was slowly added over a period of 30 minutes and stirred for 2 hours at the same temperature for completion of reaction (monitored by TLC). The reaction mass was diluted with water (800 ml) and stirred for 20 minutes for the product to precipitate out. The product was filtered, washed with water and dried under vacuum to get the title product (48 g).

Used in the preparation of phenylethanolamine derivatives as β2 adrenoreceptor agonists.

Molecular Weight:293.3
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:293.10519334
Monoisotopic Mass:293.10519334
Topological Polar Surface Area:55.4
Heavy Atom Count:22
Complexity:453
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes