2,6-Lutidine → HCID 19436797, compound

HRID 1735012Notes

Reaction equation

HRID 1735012 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH:12]=[O:13].Cl[C:15]1[N:16]=[N:17][CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:1][C:2]2[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=2[CH:12]=[O:13])[N:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 109756123-Chloro-5-methoxypyridazineHCID 178481862HCID 178481862, compound

Product 1

HCID 19436797HCID 19436797, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde (3.0 g, 0.015 mole), 3-chloro-5-methoxypyridazine (2.3 g, 0.015 mole), 2,6-lutidine (2.8 g, 0.025 mole), and toluene (80 mL) were heated in a flask equipped with a short Vigreux column until 5 mL of solvent had distilled. The mixture was then held at reflux for 4 hours, cooled, poured into 1% hydrochloric acid, and extracted with a mixture of ether and ethyl acetate. The combined extracts were washed with 1% hydrochloric acid, 1% sodium hydroxide, 5% sodium chloride, then dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate/cyclohexane to give 5-[(5-methoxy-3-pyridazinyl)oxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde (2.53 g, 55% yield) as a yellow solid.

Workup

  1. distillationhad distilled
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. additionpoured into 1% hydrochloric acid
  5. extractionextracted with a mixture of ether and ethyl acetate
  6. washThe combined extracts were washed with 1% hydrochloric acid, 1% sodium hydroxide, 5% sodium chloride
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-11f9c43f516f49d98e205346a140b853
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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