Hydroxyamine hydrochloride → 2-Oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 2413147노트

반응식

HRID 2413147 반응식
Cl[C:2]1[C:3](C=O)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[NH2:15]O.[CH:17]([O-:19])=O.[Na+]>C(O)=O>[C:3]([C:2]1[C:17](=[O:19])[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)#[N:15]

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 184670533-Chloroquinoline-2-carbaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

Where the starting material above is a 2-chloro-3-cyanoquinoline, this can be prepared by starting from an appropriate substituted acetanilide. This is heated with phosphoryl chloride and dimethylformamide to give the corresponding 2-chloro-3-quinolinecarboxaldehyde. The process involved is discussed in detail by meth-Cohn et al., J. Chem. Soc., Perkin Trans. 1, 1981, 1520. The chloroquinolinecarboxaldehyde is then reacted with hydroxylamine hydrochloride, formic acid and sodium formate with heating to give the corresponding 3-cyano-2(1H)-quinolinone. This is then heated with an excess of phosphoryl chloride to give the desired 2-chloro-3-cyanoquinoline.

후처리

  1. temperaturewith heating

출처 및 근거

ORD 기록
ord-f3baa133583e4eefada2d25af48ae68d
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04496569

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