4-Chloroaniline → HCID 18372708, compound

HRID 1069501Notes

Reaction equation

HRID 1069501 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>O>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([Cl:16])=[CH:18][CH:19]=2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 145347685-Bromo-8-hydroxyquinoline-7-carboxylic acid

Product 1

HCID 18372708HCID 18372708, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromo-8-hydroxyquinoline-7-carboxylic acid (2.68 g) of Preparation 2 and 4-chloroaniline (1.28 g) in 250 mL xylenes is heated to reflux. To this is added dropwise PCl8 (0.69 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 1.97 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-9c04faff85184ea885484fd776f49a68
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

Loading…