2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile synthesis

8synthesis methods

Product Name:2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile
CAS Number:882023-24-7
Molecular formula:C10H8N2O
Molecular Weight:172.18

Methanesulfonic acid, 1,1,1-trifluoro-, 1,2,3,4-tetrahydro-2-oxo-5-quinolinyl ester

876921-88-9
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557-21-1 Synthesis

557-21-1
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2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

882023-24-7
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Yield:882023-24-7 81%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 100; for 2 h;

Steps:

21

5-Trifluoromethanesulfonyloxy-3,4-dihydro-lH-quinolin-2-one (1.5 g) , zinc cyanide (1.3 g) and tetrakis(triphenylphosphine) palladium (0.59 g) were suspended in DMF (20 ml), and the suspension was stirred at 100°C for 2 hours.The insoluble matter was filtered off, and ethyl acetate was added to the filtrate, followed by washing with water. The resulting mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, and the residue was re?rystallized from an ethyl acetate-diethyl ether mixed solvent to thereby obtain 0.71 g (yield: 81%) of 5-cyano-3,4-dihγdro-lH- quinolin-2-one as a light brown powder.¹H-NMRtDMSO-d₆) dppm:2.45-2.60 (2H,m), 3.05(2H,t,J=7.2Hz) ,7.08-7.18(lH,m) ,7.28-7.40 (2H,m),10.37 (lH,brs)

References:

WO2006/35954,2006,A1 Location in patent:Page/Page column 197

773837-37-9 Synthesis