Dimethyl Sulfate → HCID 135731737, compound

HRID 1763227Notes

Reaction equation

HRID 1763227 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[OH:15])=[CH:6][CH:7]=1.S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:20])=[CH:10][C:9]=2[OH:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 135731740HCID 135731740, compound

Product 1

HCID 135731737HCID 135731737, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Chloro-6-(2,4-dihydroxyphenyl)pyridazine (4.0 g, 0.18 mole), dimethyl sulphate (2.55 g, 0.0201 mole), potassium carbonate (10.0 g, 0.072 mole) and dry acetone (100 ml) were stirred at room temperature for 20 hours. The reaction mixture was filtered and the inorganic residue was washed with more acetone. Evaporation of the combined filtrates gave a brown residue which was extracted with dilute sodium hydroxide solution. The aqueous extract was washed with dichloromethane, treated with charcoal, filtered and acidified. The resulting precipitate was collected, washed with water and crystallised from ethanol to give 3-chloro-6-(2-hydroxy-4-methoxyphenyl)pyridazine (2.2 g, 49%; m.p. 156°-157° ).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe inorganic residue was washed with more acetone
  3. customEvaporation of the combined filtrates
  4. customgave a brown residue which
  5. extractionwas extracted with dilute sodium hydroxide solution
  6. extractionThe aqueous extract
  7. washwas washed with dichloromethane
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. customThe resulting precipitate was collected
  11. washwashed with water
  12. customcrystallised from ethanol

Sources & evidence

ORD record
ord-baf9977647b34a539e096efe8458a488
Source dataset
uspto-grants-1978_09
Patent number
US04111935

Reaction notes

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