Dimethyl Sulfate → 3-Hydroxymethyl-1-methyl-7-trifluoromethyl-4-quinolone

HRID 325626Notes

Reaction equation

HRID 325626 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:23][OH:24].[OH-].[K+]>O.O1CCCC1>[OH:24][CH2:23][C:10]1[C:9](=[O:8])[C:18]2[C:13](=[CH:14][C:15]([C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=2)[N:12]([CH3:5])[CH:11]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178519811HCID 178519811, compound

Product 1

HCID 128078823-Hydroxymethyl-1-methyl-7-trifluoromethyl-4-quinolone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl sulphate (24.4 g.) was added over 5 minutes to a stirring solution of 4-hydroxy-3-hydroxymethyl-7-trifluoromethylquinoline (23.6 g.) and potassium hydroxide (16.3 g.) in a mixture of water (50 ml.) and tetrahydrofuran (50 ml.) at room temperature. After stirring for a further 3 hours at this temperature the solid product was collected. The filtrate was extracted with dichloromethane (3×200 ml.). The combined extracts were dried over anhydrous magnesium sulphate and evaporated to give a second crop of the solid. The combined solids were purified by high pressure liquid chromatography over silica gel, eluting with isopropanol:dichloromethane 10:90 at a flow rate of 200 ml. per minute. The same solvent was used for applying the product to silica gel. This procedure gave the novel 3-hydroxymethyl-1-methyl-7-trifluoromethyl-4-quinolone, m.p. 172°-175°.

Workup

  1. customwas collected
  2. extractionThe filtrate was extracted with dichloromethane (3×200 ml.)
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  4. customevaporated
  5. customto give a second crop of the solid
  6. customThe combined solids were purified by high pressure liquid chromatography over silica gel
  7. washeluting with isopropanol:dichloromethane 10:90 at a flow rate of 200 ml

Sources & evidence

ORD record
ord-e4e1e9f7cd034cd0a060df575ded78f8
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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