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Phosphorus oxychloride → 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

HRID 1586185
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HRID 1586185 반응식
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:22]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:22])=[C:6]2[CH:5]=[N:4]1)=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=3)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 21217703N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid

생성물 1

HCID 212177171-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of N-(1-ethylpyrazol-5-yl)-5-(methylthio) anthranilic acid (4.5 g) and POCl3 (20 ml) is refluxed overnight. The reaction mixture is poured into water, then ice is added. The mixture is extracted with CH2Cl2 and then the CH2Cl2 layer is evaporated. The residue is purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexane to afford 2.4 g of 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline, m.p. 120°-121° C.

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후처리

  1. temperatureis refluxed overnight
  2. additionice is added
  3. extractionThe mixture is extracted with CH2Cl2
  4. customthe CH2Cl2 layer is evaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with 50% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-f39cf7e402274b348654c062062d4f52
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05942520

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