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

HRID 729085Notes

Reaction equation

HRID 729085 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[NH:13][C:12](=O)[C:11]=2[CH2:10][CH2:9]1.[OH-].[Na+].P(Cl)(Cl)([Cl:27])=O>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[C:12]([Cl:27])[C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 9926017HCID 9926017, compound

Product 1

HCID 157498191-(2-Methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

Procedure

1-(2-Methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(16 g) was dissolved in phosphoryl chloride (100 ml) and heated at reflux for 5 hours. After cooling, the solution was poured onto ice, made alkaline with aqueous sodium hydroxide solution, and extracted with dichloromethane, which was dried and evaporated. Crystallisation from ethyl acetate gave 1-(2-methylphenyl)-4-chloro-6-methyl-2,3-dihydropyrrolo-[3,2-c]quinoline, which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling
  4. additionthe solution was poured onto ice
  5. extractionextracted with dichloromethane, which
  6. customwas dried
  7. customevaporated
  8. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b71226f606874ebb91d84eedf9a2d4e4
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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