Sodium Methoxide → HCID 11831960, compound

HRID 54649Notes

Reaction equation

HRID 54649 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[N:6][CH:7]=1.[CH3:18][O-:19].[Na+]>CO>[CH3:18][O:19][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117473005-Chloro-3-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 11831960HCID 11831960, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Chloro-3-[3-(trifluoromethyl)phenyl]pyridazine (4 g, 0.015 mole, Compound No. 5) and NaOMe in MeOH (16.71 g of a 25% by weight solution, 0.077 mole) were stirred at RT under N2 in MeOH (100 mL) for 4 h. The mixture was then partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), filtered and evaporated in vacuo. The crude solid was recrystallized from ethyl acetate/cyclohexane to give 5-methoxy -3-[3-(trifluoromethyl)phenyl]pyridazine (2.92 g, 74% yield, Compound No. 8) as a brown solid.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude solid was recrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-9dd6420431444e04ad580cffd06f96c9
Source dataset
uspto-grants-1997_04
Patent number
US05623072

Reaction notes

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