Dimethyl Sulfate → 8-Methoxyquinoline-5-carbaldehyde

HRID 280002Notes

Reaction equation

HRID 280002 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.C[O-].[Na+].S(OC)(O[CH3:21])(=O)=O>CS(C)=O>[CH3:21][O:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 2753638-Hydroxyquinoline-5-carbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 71762248-Methoxyquinoline-5-carbaldehydeYield 74.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.76 g (4.39 mmol) of 8-hydroxyquinoline-5-carboxaldehyde (G. R. Clemo and R. Howe, J. Chem. Soc., 1955, 3552) in 5 mL of dimethyl sulfoxide was added 0.24 g (4.4 mmol) of sodium methoxide, while keeping the mixture under nitrogen. After stirring for 5 min, 0.56 g (4.4 mmol) of dimethyl sulfate was added. The reaction was stirred for 1 hr and the solvent removed under vacuum. The residue was partitioned between dichloromethane (100 mL) and 0.5N sodium hydroxide (50 mL); the organic layer was washed with water (100 mL), dried over anhydrous magnesium sulfate, and concentrated to give 0.61 g (74%) of 8-methoxyquinoline-5-carboxaldehyde, mp 121°-122° after recrystallization from ethanol-hexane (2:25). Anal. Calcd for C11H9NO2 : C, 70.58; H, 4.85; N, 7.48. Found: C, 70.55; H, 4.91; N, 7.44.

Workup

  1. stirringThe reaction was stirred for 1 hr
  2. customthe solvent removed under vacuum
  3. customThe residue was partitioned between dichloromethane (100 mL) and 0.5N sodium hydroxide (50 mL)
  4. washthe organic layer was washed with water (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7c57d29923641f8be0c47f91aa2bb9a
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Reaction notes

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