4-Chloroaniline → HCID 9841968, compound

HRID 2415120Notes

Reaction equation

HRID 2415120 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[C:10]1[C:11](=[O:22])[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:17]=2[C:18](=[O:21])[C:19]=1[Br:20]>C(O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[C:11](=[O:22])[C:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:17]=3[C:18](=[O:21])[C:19]=2[Br:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 2559646,7-dibromoquinoline-5,8-dione

Product 1

HCID 9841968HCID 9841968, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

CeCl3 (0.1 mmol) as a catalyst and 4 equivalents of 4-chloroaniline (10 mmol) were added to 6,7-dibromo-5,8-quinolindion (10 mmol) dissolved in ethanol (100 ml). The reaction mixture was heated at reflux for 8 hrs. After reading the completion of reaction by TLC, it was cooled, filtered, and recrystallized with ethanol to give redish powder of 6-[(N-4-chlorophenyl)amino]-7-bromo-5,8-quinolidione.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 8 hrs
  3. customthe completion of reaction by TLC, it
  4. temperaturewas cooled
  5. filtrationfiltered
  6. customrecrystallized with ethanol
  7. customto give redish powder of 6-[(N-4-chlorophenyl)amino]-7-bromo-5,8-quinolidione

Sources & evidence

ORD record
ord-1cfd3e85fd6b4d18966748f1e66dcdb5
Source dataset
uspto-grants-2004_11
Patent number
US06818653B1

Reaction notes

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