Water → HCID 18372479, compound

HRID 2301420Notes

Reaction equation

HRID 2301420 reaction equation
[Cl: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.P(Cl)(Cl)Cl.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.O>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([Cl:20])=[CH:22][CH:23]=2)=[O:14])[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 78124-ChloroanilineHCID 24387Phosphorus trichlorideHCID 145347675-Chloro-8-hydroxyquinoline-7-carboxylic acid

Product 1

HCID 18372479HCID 18372479, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 5-chloro-8-hydroxyquinoline-7-carboxylic acid (0.224 g) of Preparation 3 in 50 mL xylene is heated to reflux. To this is added dropwise PCl3 (0.069 g). After 15 min, 4-chloroaniline (0.128 g) is added. 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 solid is then partitioned between EtOAc and water. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with water, dried and condensed. The crude product is recrystallized from EtOAc to yield 0.073 g of the title product as an orange solid.

Workup

  1. temperatureis heated to reflux
  2. temperatureRefluxing
  3. waitis continued overnight
  4. temperatureThe reaction is then cooled
  5. customto destroy excess PCl3
  6. customThe resulting solid is collected
  7. washwashed with water
  8. customdried
  9. customThe solid is then partitioned between EtOAc and water
  10. extractionThe aqueous layer is extracted with EtOAc (3×)
  11. washThe combined organic layers are washed with water
  12. customdried
  13. customcondensed
  14. customThe crude product is recrystallized from EtOAc

Sources & evidence

ORD record
ord-02b486cb31c545c199dea7c397f33ed2
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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