Hydrogen Bromide → 4-Chloro-2-methylquinolin-6-ol

HRID 1720269Notes

Reaction equation

HRID 1720269 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]=[C:4]([CH3:14])[CH:3]=1.Br>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6101144-Chloro-6-methoxy-2-methylquinoline

Product 1

HCID 7715204-Chloro-2-methylquinolin-6-olYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere in a 500 single-neck round bottom flask equipped with a condenser and a magnetic stirrer, a solution of 2.00 g (9.62 mmol) of 4-chloro-6-methoxy-2-methylquinoline and 150 mL of 48% hydrobromic acid was heated under reflux for 90 minutes. Upon cooling to room temperature, the reaction solution was evaporated under reduced pressure to afford a solid residue. The residue was slurried in chloroform filtered and washed with chloroform. The solid was next slurried in a mixture of saturated aqueous sodium carbonate and ethyl acetate for 15 minutes, filtered and washed successively with saturated aqueous sodium carbonate, water and ethyl acetate. After air drying there was obtained 741 mg (40%) of 4-chloro-2-methylquinolin-6-ol: m.p. 233° C.

Workup

  1. customUnder a nitrogen atmosphere in a 500 single-neck round bottom flask equipped with a condenser and a magnetic stirrer
  2. temperatureunder reflux for 90 minutes
  3. customthe reaction solution was evaporated under reduced pressure
  4. customto afford a solid residue
  5. filtrationfiltered
  6. washwashed with chloroform
  7. additionThe solid was next slurried in a mixture of saturated aqueous sodium carbonate and ethyl acetate for 15 minutes
  8. filtrationfiltered
  9. washwashed successively with saturated aqueous sodium carbonate, water and ethyl acetate
  10. customAfter air drying there

Sources & evidence

ORD record
ord-2f0451c9f9844b3f9a5ab269a273219d
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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