Phosphorus oxychloride → 2-Chloroquinolin-8-ol

HRID 730733Notes

Reaction equation

HRID 730733 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:15])=O>[NH4+].[OH-]>[Cl:15][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515617HCID 178515617, compound

Product 1

HCID 2748782-Chloroquinolin-8-ol

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,8-dihydroxyquinoline (4 g, 24.8 mmol, Fluka) and phosphorus oxychloride (20 mL, Aldrich) was stirred at 100° C. for 1 h. The clear solution was cooled to room temperature and poured slowly with stirring into a mixture of NH4OH (150 mL) and crushed ice (200 g). The white solid that precipitated was filtered, dissolved in concentrated HCl (200 mL) and stirred at 100° C. for 1 h. Neutralization of the cooled to room temperature acid solution with NH4OH afforded white precipitate, which was filtered, washed with water and dried to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 180 (M+1).

Workup

  1. temperatureThe clear solution was cooled to room temperature
  2. additionpoured slowly
  3. customThe white solid that precipitated
  4. filtrationwas filtered
  5. dissolutiondissolved in concentrated HCl (200 mL)
  6. stirringstirred at 100° C. for 1 h
  7. temperatureNeutralization of the cooled to room temperature acid solution with NH4OH afforded white precipitate, which
  8. filtrationwas filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-de19be1e8d5a4ca0b95dd33164587ac9
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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