Dimethyl Sulfate → HCID 178493572, compound

HRID 2415124Notes

Reaction equation

HRID 2415124 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 178493572HCID 178493572, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A slurry of 2,4-dihydroxyquinoline (20.7 g, 0.13 mol), potassium carbonate (35.5 g, 0.26 mol), and dimethyl sulfate (14.6 ml, 0.15 mol) in acetone (800 ml) was heated at reflux for 3 days. The reaction was cooled to ambient temperature then evaporated under reduced pressure. The residue was slurried in a system of water (1000 ml) and ethyl acetate (500 ml) for 1 hour. The solids were collected then rinsed with water (3×250 ml) and ethyl ether (3×250 ml). Vacuum dried over phosphorus pentoxide to give 2-hydroxy4-methoxyquinoline (16.3 g, 72%) as a tan powder. [M+H]+ 176, M+CH3CN=217.

Workup

  1. temperatureat reflux for 3 days
  2. customthen evaporated under reduced pressure
  3. customThe solids were collected
  4. washthen rinsed with water (3×250 ml) and ethyl ether (3×250 ml)
  5. dry with materialVacuum dried over phosphorus pentoxide

Sources & evidence

ORD record
ord-1656a04dc8144b59a07685fc93d29b7c
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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