Hydrazine hydrate (1:1) → HCID 14441180, compound

HRID 1110780Notes

Reaction equation

HRID 1110780 reaction equation
C1(=O)N(CC[C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)C(=O)C2=CC=CC=C12.O.[NH2:20]N.[O:22]=[C:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([O:30]C1C=CC=CC=1)=O.[C:37]1([CH3:43])C=CC=CC=1.C(OCC)(=O)C>CO>[N:9]1([CH2:43][CH2:37][NH:20][C:28]([N:24]2[CH2:25][CH2:26][CH2:27][C:23]2=[O:22])=[O:30])[CH:8]=[CH:12][CH:11]=[N:10]1

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 144410901-Phenoxycarbonyl-2-oxopyrrolidineHCID 21584019Toluene ethylacetateHCID 178514984HCID 178514984, compound

Product 1

HCID 14441180HCID 14441180, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.58 g (14.8 mmol) of 2-phthalimidoethylpyrazole in 45 ml of methanol was added 1.11 g (22.2 mmol) of hydrazine hydrate, and the mixture was refluxed for 7 hr. The solvent was evaporated under reduced pressure, and the residue was washed with CH2Cl2 and ethyl acetate, and filtered. The filtrate was evaporated under reduced pressure, and then 2.73 g (13.3 mmol) of 2-oxo-1-phenoxycarbonylpyrrolidine (II) was added to the residue, and the mixture was heated at 115°-120° C. for 3 hr. After cooling, the reaction mixture was refined by silica gel column chromatography, and the resulting crystalline product obtained from the eluate with toluene/ethyl acetate (3/1-1/1 v/v) was recrystallized from ether, whereby 1.91 g (64.7%) of the objective compound (I a-38) melting at 62.5°-63.5° C. was obtained.

Workup

  1. temperaturethe mixture was refluxed for 7 hr
  2. customThe solvent was evaporated under reduced pressure
  3. washthe residue was washed with CH2Cl2 and ethyl acetate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. temperaturethe mixture was heated at 115°-120° C. for 3 hr
  7. temperatureAfter cooling
  8. customwas recrystallized from ether

Sources & evidence

ORD record
ord-3bbf81dce1484306ac7360e340dcb1f9
Source dataset
uspto-grants-1990_12
Patent number
US04977167

Reaction notes

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