Water → 6-[3-(Trifluoromethyl)phenyl]-4-pyridazinecarboxylic acid ethyl ester

HRID 52770Notes

Reaction equation

HRID 52770 reaction equation
N1([CH:7]2[N:12](C(OCC)=O)[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH:9]=[C:8]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])CCOCC1.O>CN(C=O)C>[CH2:31]([O:30][C:28]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[N:11]=[N:12][CH:7]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 962WaterHCID 117980206-(4-morpholinyl)-3-[3-(trifluoromethyl)phenyl]-1,5(6H)-pyridazindicarboxylic acid diethyl ester

Product 1

HCID 106376556-[3-(Trifluoromethyl)phenyl]-4-pyridazinecarboxylic acid ethyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(4-morpholinyl)-3-[3-(trifluoromethyl)phenyl]-1,5(6H)-pyridazindicarboxylic acid, diethyl ester (10.73 g, 0.024 mole) was refluxed in DMF (150 mL) for 30 min. The mixture was poured into water and extracted 3×100 mL with ethyl acetate. The organic layer was dried (MgSO4), filtered through silica gel, and evaporated in vacuo to give a crude solid which was recrystallized from cyclohexane/ethyl acetate to give 6-[3-(trifluoromethyl)phenyl]-4-pyridazinecarboxylic acid ethyl ester (3.34 g, 47% yield, Compound No. 1) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-6b2b8b24a609402ca8aa97326e39ae6e
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Reaction notes

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