Hydrochloric Acid → [6-(3-Chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanol

HRID 891947Notes

Reaction equation

HRID 891947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([CH2:15][O:16]COC)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.O.C(OCC)(=O)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 22240138HCID 22240138, compound

Product 1

HCID 22240129[6-(3-Chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanolYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(3-Chloro-4-fluoro-phenyl)-5-methoxymethoxymethyl-pyridazine (0.06 g, 0.21 mmol) was dissolved in dioxane (2 ml) and treated with 1N HCl (0.2 ml, 0.2 mmol). The reaction mixture was refluxed for 1.5 hours then cooled to room temperature. Water and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 1:1 then 2:8) to provide [6-(3-chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanol (13 mg, 26%) as a light yellow solid, MS: m/e=239.2 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel (hexane-ethylacetate 1:1

Sources & evidence

ORD record
ord-18131378fce447d2b10a6396fc58823d
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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