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

HRID 729083Notes

Reaction equation

HRID 729083 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-d90e245ec69c4604a680eee94b281720
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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