Sodium Hydroxide → HCID 66875509, compound

HRID 2381483Notes

Reaction equation

HRID 2381483 reaction equation
Cl[C:2]1[C:3](=[O:19])[NH:4][N:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:17])[F:16].[OH-].[Na+].[H][H]>[Pd].C(Cl)Cl.O>[F:17][C:15]([F:16])([F:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[N:5][NH:4][C:3](=[O:19])[CH:2]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 668755114-chloro-5-(2-trifluoromethyl-phenoxy)-2H-pyridazin-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 66875509HCID 66875509, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A pressure vial containing a mixture of 4-chloro-5-(2-trifluoromethyl-phenoxy)-2H-pyridazin-3-one (3.66 g, 12.59 mmol), water (70 mL), and a 2N aqueous sodium hydroxide solution (7 mL, 14 mmol) was treated with 10% palladium on carbon (0.37 mg, 10% weight of 4-chloro-5-(2-trifluoromethyl-phenoxy)-2H-pyridazin-3-one). The reaction was then pressurized with hydrogen (50 psi), where it shook for 4 d. The resulting reaction mixture was diluted with methylene chloride (100 mL) and water (100 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo. The aqueous residue was acidified with a 2N aqueous hydrochloric acid solution and was then extracted with a 90/10 methylene chloride/methanol solution. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel column chromatography (ISCO, 120 g, 50%-70% ethyl acetate/hexanes) afforded 5-(2-trifluoromethyl-phenoxy)-2H-pyridazin-3-one (2.26 g, 70%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.79 (d, J=2.7 Hz, 1H), 7.52-7.60 (m, 2H), 7.82 (t, J=8.5 Hz, 1H), 7.89 (d, J=8.2 Hz, 1H), 8.00 (d, J=2.7 Hz, 1H), 13.04 (br. s., 1H).

Workup

  1. additionA pressure vial containing
  2. customThe resulting reaction mixture
  3. filtrationfiltered through a pad of diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionwas then extracted with a 90/10 methylene chloride/methanol solution
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2796a9c19f65469283a7e534b8785a4b
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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