6-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Off-white solid

2) To the 98 g of the product of the step 1), N-(4-methoxyphenyl)-3-chloroacrylamide, 500 ml of tetrahydrofuran and 98 g of palladium chloride were added.Under 5 kg pressure, Warming up to 100 to 110 ° C for 3 hours, after cooling to room temperature, Filtration and complete spin-drying to give the crude 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone;3) The crude 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone obtained in the step 3) was recrystallized from 50 ml of ethanol, and the activated carbon was decolorized.Filtration gave 74 g of 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone as an off-white solid, yield 95percent.The total yield was 85percent.Step 2:Into a 2 L three-necked flask, 96.1 g (0.45 mol) of N- (4'-methoxyphenyl) -3-chloropropanamide and150g (2.05mol) N, N-dimethylacetamide to start stirring, To the system was added 240.0 g (1.8 mol) of aluminum trichloride, Plus Bi, warmed to 150 , incubated for 2h, TLC detection reaction was completed, stirred and cooled to 60 , To the system slowly added 1500g ice water quench, Precipitated product, filtered, and the resulting crude product was recrystallized from 1000 mL of ethanol, 63.5 g of a white-like solid was obtained, Namely 6-hydroxy-3, 4-dihydroquinolin-2-one, Yield 86.5percent (4-methoxyaniline yield 76.5percent), purity99.20percent.2) To the 98 g of the product of the step 1), N-(4-ethoxyphenyl)-3-chloroacrylamide, 500 ml of tetrahydrofuran and 98 g of palladium chloride were added.Under the pressure of 5 kg, the temperature was raised to 100 to 110 ° C for 3 hours, and after cooling to room temperature, Filtration and complete spin-drying to give the crude 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone;3) The crude 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone obtained in the step 3) was recrystallized from 50 ml of ethanol, and the activated carbon was decolorized.Filtration gave 74 g of 6-hydroxy-3, 4-dihydro-2(1H)-quinolinone as an off-white solid, yield 87percent.The total yield was 75percent.p-Aminophenol [0.5 gm (4.58 mmol)] was dissolved in 30 ml of each methylene chloride and saturated aqueous bicarbonate solution and stirred for 5 minutes at ambient temperature. 3-Chloropropionyl chloride [0.49 ml (5.04 mmol.)] was added over 10 min. and the reaction mixture was stirred at ambient temperature for 4 hrs. A large amount of precipitate was observed. The solids were filtered and dried to afford 0.82 gm ( 90 percent) of an off-white solid. MS APCI m/e 200 (p+1). This product (0.82 gm (4.1 mmol.)) was combined with 1.6 gm (12.3 mmol.) aluminum chloride as a mixture of solids. The mixture was then heated in an oil bath at 210 °C for 10 minutes or until the gas evolution ceases. The reaction mixture was then allowed to cool to ambient temperature and then quenched in an ice/water mixture. The aqueous phase was extracted with ethyl acetate which was separated, dried over sodium sulfate and evaporated in vacuo to a light brown solid 0.58 gm (87 percent) MS APCI m/e 164 (p+1).

A metabolite of Cilostazole.

Molecular Weight:163.17
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:163.063328530
Monoisotopic Mass:163.063328530
Topological Polar Surface Area:49.3
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes