Hydrazine hydrate (1:1) → 6-(3-trifluoromethyl-4-morpholino-phenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 65193Notes

Reaction equation

HRID 65193 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH:13]([CH3:17])C(O)=O)=O)=[CH:9][C:8]=2[C:20]([F:23])([F:22])[F:21])[CH2:3][CH2:2]1.[N:24]1([C:30](N)=[O:31])CCOCC1.O.[NH2:34]N>C(O)(=O)C>[F:23][C:20]([F:21])([F:22])[C:8]1[CH:9]=[C:10]([C:11]2[CH2:13][CH2:17][C:30](=[O:31])[NH:24][N:34]=2)[CH:18]=[CH:19][C:7]=1[N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70480463HCID 70480463, compound

Product 1

HCID 202103096-(3-trifluoromethyl-4-morpholino-phenyl)-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.8 g of 4-morpholino-3-trifluoromethylbenzoylpropionic acid-morpholineamide together with 2.2 ml of hydrazine hydrate and 90 ml of 50% acetic acid are refluxed for 1 hour. The reaction mixture is cooled, concentrated in a rotary evaporator, and a small amount of water is added; the pH-value is adjusted to 6 with a 2 N sodium carbonate solution, and the mixture is extracted with methylene chloride. The methylene chloride extracts are washed with water, dried over sodium sulfate and concentrated by evaporation. From the residue is obtained, by recrystallisation from ethanol/petroleum ether, 6-(3-trifluoromethyl-4-morpholino-phenyl)-4,5-dihydro-3(2H)-pyridazinone, m.p. 163°-166° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated in a rotary evaporator
  3. additiona small amount of water is added
  4. extractionthe mixture is extracted with methylene chloride
  5. washThe methylene chloride extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5e41a58e917648b5ae23f6d9ffc1d1bd
Source dataset
uspto-grants-1986_09
Patent number
US04613599

Reaction notes

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