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

HRID 1069500Notes

Reaction equation

HRID 1069500 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 PCl. 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 PCl
  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-b824ec3e6003421dbbb60351e9342d67
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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