Acetic Acid → 2-Oxo-1,2-dihydroquinoline-3-carbonitrile
Reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)(=[O:16])C>Cl>[C:12]([C:11]1[C:2](=[O:16])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Alternatively, the acetanilide can be heated with dimethylformamide, phosphoryl chloride and hydroxylamine hydrochloride to give a 2-chloro-3-cyanoquinoline. This process is a particularly convenient method for obtaining the chlorocyanoquinoline directly from an acetanilide. The indicated chloro-cyano-compound can then be hydrolyzed either under acidic or basic conditions to give the corresponding desired 3-cyano-2(1H)-quinolinone. Specifically, if the 2-chloro-3-cyanoquinoline is boiled in acetic acid for 1 hour or refluxed in 4N hydrochloric acid for 10-15 minutes, the corresponding 3-cyano-2(1H)-quinolinone is obtained.
Sources & evidence
- ORD record
- ord-dbafeb1532fc4d5586b24ec044153393
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04735948
Reaction notes
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