4,7-Dichloroquinoline → HCID 19738138, compound

HRID 2255432Notes

Reaction equation

HRID 2255432 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C(OCC)(=O)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:18][C:17]3[CH:19]=[CH:20][C:14]([F:13])=[CH:15][CH:16]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 97314-Fluoroaniline

Product 1

HCID 19738138HCID 19738138, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To 2.0 g of 4,7-dichloroquinoline was added 2.24 g of 4-fluoroaniline, and the mixture was heated with stirring to 160° C. After a few minutes at this temperature, the mixture smoked and the melt solidified. The solid was allowed to cool and was then dissolved in ethyl acetate and washed to remove the aniline. The organic layer was dried over MgSO4 and then solvent was removed using reduced pressure. The residue was recrystallized in heptane to yield 1.27 g of 7-chloro-N-(4-fluorophenyl)-4-quinolinamine. M.P. 214°-16° C. (46.1% yield).

Workup

  1. temperaturethe mixture was heated
  2. waitAfter a few minutes at this temperature
  3. temperatureto cool
  4. washwashed
  5. customto remove the aniline
  6. dry with materialThe organic layer was dried over MgSO4
  7. customsolvent was removed
  8. customThe residue was recrystallized in heptane

Sources & evidence

ORD record
ord-35aa06d05517449d9d28015946ac6f6a
Source dataset
uspto-grants-1993_08
Patent number
US05240940

Reaction notes

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