Acetic Acid → 2-Oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 648443

반응식

HRID 648443 반응식
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]

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 115646012-Chloroquinoline-3-carbonitrile

생성물 1

HCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-dbafeb1532fc4d5586b24ec044153393
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04735948

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