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

HRID 729083ノート

反応式

HRID 729083 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-d90e245ec69c4604a680eee94b281720
出典データセット
uspto-grants-1991_09
特許番号
US05051508

反応ノート

読み込み中…