Hydrochloric Acid → HCID 12807840, compound

HRID 543702Notes

Reaction equation

HRID 543702 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12][S:13]([CH3:15])=[O:14].[OH-].[K+].S(OC)(O[CH3:22])(=O)=O.Cl>O>[CH3:22][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2](=[O:1])[C:3]([CH2:12][S:13]([CH3:15])=[O:14])=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178504631HCID 178504631, compound

Product 1

HCID 12807840HCID 12807840, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-hydroxy-3-methylsulphinylmethylquinoline (4.4 g.) and potassium hydroxide (1.68 g.) in water (20 ml.) at 0°-5° was added dimethyl sulphate (2.52 g.). The solution was stirred at room temperature for 30 minutes, then neutralised with 5 N aqueous hydrochloric acid. The resultant sticky solid was triturated with industrial methylated spirit to give a solid product. The product was purified by high pressure liquid chromatography over silica gel, eluting with isopropanol:dichloromethane 95:5 at a flow rate of 200 ml. per minute. This procedure gave the novel 1-methyl-3-methylsulphinylmethyl-4-quinolone, m.p. 94°-96°.

Workup

  1. customThe resultant sticky solid was triturated with industrial methylated spirit
  2. customto give a solid product
  3. customThe product was purified by high pressure liquid chromatography over silica gel
  4. washeluting with isopropanol:dichloromethane 95:5 at a flow rate of 200 ml

Sources & evidence

ORD record
ord-eafe3da34fdb4681b75ca3e48dc8601c
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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