Sodium Hydroxide → 1-(2-Methoxyphenyl)-4-chloro-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729083노트

반응식

HRID 729083 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1.[OH-].[Na+].P(Cl)(Cl)([Cl:29])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[N:14]=[C:13]([Cl:29])[C:12]=2[CH2:11][CH2:10]1

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 157498161-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

생성물 1

HCID 157498171-(2-Methoxyphenyl)-4-chloro-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline

실험 절차

1-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (9.55 g) was dissolved in phosphoryl chloride (100 ml) and heated at reflux for 2.5 hours. After cooling, the solution was poured onto ice, made alkaline with aqueous sodium hydroxide solution, and extracted with dichloromethane. The organic extract was dried and evaporated, and the crude product purified by chromatography (silica gel, 50-100% diethyl ether in petroleum ether). The first compound to elute was 4-chloro-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline, m.p. 99°-101°. Later fractions containing the desired product were recrystallised from ethyl acetate, then ethyl acetate/ethanol to give1-(2-methoxyphenyl)-4-chloro-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline, m.p. 183°-184°.

후처리

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter cooling
  4. additionthe solution was poured onto ice
  5. extractionextracted with dichloromethane
  6. extractionThe organic extract
  7. customwas dried
  8. customevaporated
  9. customthe crude product purified by chromatography (silica gel, 50-100% diethyl ether in petroleum ether)
  10. washThe first compound to elute
  11. additionLater fractions containing the desired product
  12. customwere recrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-d90e245ec69c4604a680eee94b281720
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051508

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