Sodium Bicarbonate → 6-CHLORO-8-HYDROXYQUINOLINE

HRID 2048066Notes

Reaction equation

HRID 2048066 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12]C)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 580424696-Chloro-8-methoxyquinoline

Product 1

HCID 3841626-CHLORO-8-HYDROXYQUINOLINEYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

6-Chloro-8-methoxyquinoline (Preparation 43, 10 g, 51.6 mmol) was added to pyridine hydrochloride (43 g, 375 mmol) and the mixture heated at 150° C. 1 hour. The reaction mixture was diluted with water (200 mL), basified to pH=8 with saturated aqueous sodium bicarbonate solution, filtered and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 5 to 10% EtOAc in petroleum ether to yield the title compound as a pale yellow solid (5.6 g, 70%):

Workup

  1. custom1 hour
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude product was purified with silica gel chromatography
  5. washeluting with 5 to 10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-02e8269a3f5c4e9fa4f7c6acf881ebcd
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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