Potassium Carbonate → 6-(Trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one

HRID 877221Notes

Reaction equation

HRID 877221 reaction equation
O=C1O[C:5]([CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=O)([C:7]([F:10])([F:9])[F:8])[N:4]=C1C(C)C.Cl.[NH2:24]N.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[F:8][C:7]([F:10])([F:9])[C:5]1[CH2:11][CH2:12][C:13](=[O:15])[NH:24][N:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115031Hydrazinium chlorideHCID 66933100HCID 66933100, compound

Product 1

HCID 497606526-(Trifluoromethyl)-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

8.44 g (26.1 mmol) of tert-butyl 3-[5-oxo-4-(propan-2-yl)-2-(trifluoromethyl)-2,5-dihydro-1,3-oxazol-2-yl]propanoate [CAS Reg. No. 87341-14-8] and 13.44 g (130.5 mmol) of hydrazine hydrochloride were stirred in 100 ml of glacial acetic acid at 118° C. for 2 hours. The reaction solution was then evaporated to dryness under reduced pressure. The residue obtained was taken up in 100 ml of water and made basic using potassium carbonate. The basic solution was subsequently extracted three times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to dryness. The crude product was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 50:1→10:1). This gave 2.65 g (15.95 mmol, 61% of theory) of the title compound.

Workup

  1. customThe reaction solution was then evaporated to dryness under reduced pressure
  2. customThe residue obtained
  3. extractionThe basic solution was subsequently extracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 50:1→10:1)

Sources & evidence

ORD record
ord-86a42abebece464fb4a459107c6e36bb
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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