Hydrochloric Acid → 6-[3-(Trifluoromethyl)phenyl]-4-pyridazinol

HRID 52774Notes

Reaction equation

HRID 52774 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.[OH-:18].[Na+].Cl>CS(C)=O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([C:4]2[N:5]=[N:6][CH:7]=[C:2]([OH:18])[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117473005-Chloro-3-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 1785168066-[3-(Trifluoromethyl)phenyl]-4-pyridazinolYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-3-[3-(trifluoromethyl)phenyl]pyridazine (2 g, 0.0077 mole, Compound No. 5), 2.5N NaOH (50 mL) and DMSO (100 mL) were refluxed under N2 for 2 h. The mixture was then allowed to cool and made acidic with 12N HCl and extracted 3×100 mL with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give a crude solid which was recrystallized from methanol to give 6-[3-(trifluoromethyl)phenyl]-4-pyridazinol (1 g, 54% yield, Compound No. 25) as a light brown solid.

Workup

  1. temperatureto cool
  2. extractionextracted 3×100 mL with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a crude solid which
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-b795f8dddaf541d182cd355a949d854b
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Reaction notes

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