Chlorine monoxide → 6-chloro-3-methyl-7H-indeno[2,1-c]quinoline-7-on

HRID 377590Notes

Reaction equation

HRID 377590 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[C:7]=3[C:8](=O)[NH:9]2)=[CH:4][CH:3]=1.O(Cl)[Cl:22]>>[Cl:22][C:8]1[C:7]2[C:13](=[O:20])[C:14]3[C:19]([C:6]=2[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

3

Reactant 2

HCID 24646Chlorine monoxideHCID 19356120HCID 19356120, compound

Product 1

HCID 193561186-chloro-3-methyl-7H-indeno[2,1-c]quinoline-7-onYield 73.4%

Procedure

A mixture of 3-methyl-5H-indeno[2,1-c]quinoline-6,7-dion obtained in reference example 5 (700 mg, 2.7 mmol) and phophorous oxychloride (10 ml, 107 mmol) was refluxed with heat for 1.5 hours. The reaction mixture was distilled to dryness. To the residue was added water to obtain a crystal precipitated by filtration. The crystal obtained was washed with water and dissolved in chloroform to filter off undissolved substances. Recrystallization from benzene to give 550 mg (yield 73.4%) of the title compound. m.p.: 208-211° C. 1H-NMR(CDCl3) δ: 8.38(1H, d, J=9 Hz), 8.13(1H, d, J=7 Hz), 7.85(1H, s), 7.80(1H, d, J=6 Hz), 7.64(1H, d-d-d, J=8,8,1 Hz), 7.56-7.50(2H, m), 2.60(3H, s). IR(KBr)cm-1 : 1718, 1623, 1557, 1494, 1460, 1413, 1064, 915, 867, 755, 715.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heat for 1.5 hours
  3. distillationThe reaction mixture was distilled to dryness
  4. additionTo the residue was added water
  5. customto obtain a crystal
  6. customprecipitated by filtration
  7. customThe crystal obtained
  8. washwas washed with water
  9. dissolutiondissolved in chloroform
  10. filtrationto filter off undissolved substances
  11. customRecrystallization from benzene

Sources & evidence

ORD record
ord-4a5e8bf94e1d42db9b40b6beac77f53f
Source dataset
uspto-grants-2000_02
Patent number
US06028079

Reaction notes

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