Dimethylformamide → 2-Oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

HRID 1811399Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][C:11](=[O:17])[NH:12]2)(=O)=O.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][C:11](=[O:17])[NH:12]2)#[N:21]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Trifluoromethanesulfonyloxy-3,4-dihydro-1H-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 recrystallized from an ethyl acetate-diethyl ether mixed solvent to thereby obtain 0.71 g (yield: 81%) of 5-cyano-3,4-dihydro-1H-quinolin-2-one as a light brown powder.

Workup

filtrationThe insoluble matter was filtered off
additionethyl acetate was added to the filtrate
washby washing with water
dry with materialThe resulting mixture was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customthe residue was recrystallized from an ethyl acetate-diethyl ether mixed solvent

Sources & evidence

ORD record: ord-59ad4e24ccf44b7089679d6188e583e5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362252B2

Reaction notes

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