Methanol → HCID 136379420, compound

HRID 1019973Notes

Reaction equation

HRID 1019973 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+].CO>C(OCC)(=O)C>[CH3:13][O:14][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 1354277102-Chloro-quinolin-7-ol

Product 1

HCID 136379420HCID 136379420, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-quinolin-7-ol (4.2 g, 23.4 mmol, 1.0 eq) is added at room temperature to a stirred solution of sodium methoxide in methanol (15% weight, 200 mL, 561.6 mmol, 24.0 eq) and the resulting mixture is heated under reflux for 20 hours. Solvent is removed, the residue is dissolved in water (50 mL) and neutralized with acetic acid, followed by extraction with ethyl acetate (3×50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 6:1, v/v) to afford 2-methoxy-quinolin-7-ol as a yellow solid (3.3 g, 79% yield).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 20 hours
  3. customSolvent is removed
  4. dissolutionthe residue is dissolved in water (50 mL)
  5. extractionfollowed by extraction with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organic layers are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude product that
  10. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-56c89d13ba8a42359776d32da2d66a81
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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