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

HRID 1456014노트

반응식

HRID 1456014 반응식
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].O=P(Cl)(Cl)[Cl:20]>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:10]([C:11]([Cl:20])=[C:6]2[CH:5]=[N:4]1)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH3:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 154274682-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acid

생성물 1

HCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline수율 68.3%

실험 절차

A mixture of N-(1-ethylpyrazol-5-yl)anthranilic acid (278 g, 1.2 mol) and POCl3 (550 g, 3.6 mol) was refluxed for 3 hours. The reaction mixture was cooled and then was poured into ice/water (3-4 L) . A solid formed which was collected by filtration and washed with water. The filtrate was extracted with CH2Cl2 (1 L) and the CH2Cl2 layer was evaporated to about 50 ml and both this solution and the previously isolated solid were purified by column chromatography on silica gel eluting with CH2Cl2 to afford 190 g (68%) of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline.

후처리

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customA solid formed which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. extractionThe filtrate was extracted with CH2Cl2 (1 L)
  7. customthe CH2Cl2 layer was evaporated to about 50 ml and both this solution
  8. customthe previously isolated solid were purified by column chromatography on silica gel eluting with CH2Cl2

출처 및 근거

ORD 기록
ord-15e7fcc8ab484cfe81800c675a2327d2
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843956

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