Phosphorus oxychloride → 1-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

HRID 729092Notes

Reaction equation

HRID 729092 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[CH:10]=[CH:9]1.P(Cl)(Cl)([Cl:25])=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:25])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 157498281-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline

Product 1

HCID 157498291-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

Procedure

1-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline (4.75 g) and phosphoryl chloride (40 ml) were heated at reflux for 1.5 hours. The phosphoryl chloride was evaporated in vacuo, the residue poured onto ice and extracted with dichloromethane, which was dried and evaporated. Crystallisation from ethanol yielded 1-(2-methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline (4.76 g), m.p.135°-137°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe phosphoryl chloride was evaporated in vacuo
  3. additionthe residue poured onto ice
  4. extractionextracted with dichloromethane, which
  5. customwas dried
  6. customevaporated
  7. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-6b4fdbaed67c49c7a3c3280d452a3774
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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