Sodium Methoxide → HCID 11831960, compound

HRID 52773Notes

Reaction equation

HRID 52773 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-507926b883f14172b3c1750a4b34b6df
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Reaction notes

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