Dimethyl Sulfate → HCID 21435012, compound

HRID 267521Notes

Reaction equation

HRID 267521 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([OH:18])=[O:17])=[CH:5]1.S(OC)(O[CH3:23])(=O)=O>C(O)C.[OH-].[Na+]>[CH3:23][O:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=2)[C:7](=[O:15])[C:6]([C:16]([OH:18])=[O:17])=[CH:5]1

Participants

5

Reactant 2

HCID 6497Dimethyl Sulfate2×HCID 21435001HCID 21435001, compound

Product 1

HCID 21435012HCID 21435012, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

1,4-Dihydro-1-(2-hydroxyethyl)-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (1 g) in ethanol (30 ml) and aqueous sodium hydroxide (10 ml, 40%) was treated alternatively with dimethyl sulphate (5 ml) and aqueous sodium hydroxide (10 ml, 40 %) until dimethylsulphate (25 ml) had been added. The mixture was refluxed for 1.5 hours and concentrated to a volume of 20 ml. Concentrated hydrochloric acid was added and the solid was collected and washed with water and dried. The product had m.p. 244°-245° (d).

Workup

  1. additionhad been added
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. concentrationconcentrated to a volume of 20 ml
  4. additionConcentrated hydrochloric acid was added
  5. customthe solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ad5c982d4c574bd8bff20d550315904d
Source dataset
uspto-grants-1976_03
Patent number
US03943141

Reaction notes

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