Sodium methanesulfinate → HCID 12807841, compound

HRID 543700Notes

Reaction equation

HRID 543700 reaction equation
Cl.Cl[CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:15])[CH:5]=1.[CH3:16][S:17]([O-:19])=[O:18].[Na+]>CN(C)C=O>[CH3:15][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[C:4]([CH2:3][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:5]1

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 13669337HCID 13669337, compound

Product 1

HCID 12807841HCID 12807841, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloromethyl-1-methyl-4-quinolone hydrochloride (2.0 g.) was added portionwise during 1 minute to a stirred suspension of sodium methanesulphinate (5.0 g.) in anhydrous dimethylformamide (70 ml.) at room temperature. The mixture was stirred at this temperature for 16 hours, then evaporated to dryness. The residue was triturated with water (50 ml.), filtered, the filtrate basified with aqueous sodium hydroxide and then extracted with dichloromethane (2×50 ml.). The combined extracts were dried over anhydrous magnesium sulphate and evaporated to give the novel 1-methyl-3-methylsulphonylmethyl-4-quinolone, m.p. 201°-204° (from acetone).

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with water (50 ml.)
  3. filtrationfiltered
  4. extractionextracted with dichloromethane (2×50 ml.)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-f3c7cfa2f79c4f1fac0db0e6be58481e
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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