4-Chloroaniline → N-(4-Chlorophenyl)-8-hydroxy-7-quinolinecarboxamide

HRID 382861Notes

Reaction equation

HRID 382861 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.P(Cl)(Cl)Cl>O>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:12]([C:3]2[C:2]([OH:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][CH:4]=2)=[O:14])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 24387Phosphorus trichlorideHCID 2313638-Hydroxyquinoline-7-carboxylic Acid

Product 1

HCID 18372520N-(4-Chlorophenyl)-8-hydroxy-7-quinolinecarboxamideYield 32.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-hydroxyquinoline-7-carboxylic acid (3.78 g) of Preparation 1 and 4-chloroaniline (2.55 g) in 250 mL xylenes is heated to reflux. To this is added dropwise PCl3 (1.37 g). Refluxing is continued overnight. The reaction is then cooled and water is added to destroy excess PCl3. The resulting solid is collected, washed with water and dried. The crude product is recrystallized from EtOAc/hexanes to yield 1.96 g of the title product as an orange solid.

Workup

  1. temperatureis heated to reflux
  2. temperatureRefluxing
  3. temperatureThe reaction is then cooled
  4. customto destroy excess PCl3
  5. customThe resulting solid is collected
  6. washwashed with water
  7. customdried
  8. customThe crude product is recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-3dc46ab04c534ae0b46a7a1f71ba2db6
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Reaction notes

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