Phosphorus trichloride → MW88KT29DZ

HRID 2301407Notes

Reaction equation

HRID 2301407 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:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.P(Cl)(Cl)Cl>O>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][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 24387Phosphorus trichlorideHCID 660364-ChlorobenzylamineHCID 2313638-Hydroxyquinoline-7-carboxylic Acid

Product 1

HCID 10470802MW88KT29DZYield 21.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-hydroxyquinoline-7-carboxylic acid (0.250 g) of Preparation 1 and 4-chlorobenzylamine (0.187 g) in 25 mL xylenes is heated to reflux. To this is added dropwise PCl3 (0.073 g). Refluxing is continued overnight. The reaction is then cooled and water is added to destroy excess PCl3. The resulting solid is collected and recrystallized from EtOAc/hexanes to yield 0.088 g of the title product as a yellow 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. customrecrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-8a91f75189cd400f87946e84d1a639a4
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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