Hydrogen Bromide → 4-Chloroquinolin-6-ol

HRID 1720276Notes

Reaction equation

HRID 1720276 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.Br.[OH-].[Na+]>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 2283484-Chloro-6-methoxyquinoline

Product 1

HCID 184331324-Chloroquinolin-6-olYield 56.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.99 g (18.1 mmol) of 4-chloro-6-methoxyquinoline and 50 mL of 48% hydrobromic acid is heated under reflux for seven hours. Upon cooling to room temperature, the reaction solution afforded a dark solid that was then slurried in water. The aqueous mixture was adjusted to pH 10 by the addition of 4N sodium hydroxide. The resulting solid was filtered, washed with water and air-dried to give 1.83 g (56%) of 4-chloroquinolin-6-ol: m.p. 223° C.

Workup

  1. temperatureunder reflux for seven hours
  2. customthe reaction solution afforded a dark solid
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-c0fdfe9b5da74a6c90547c030d1edfe9
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

Loading…