Hydrazine hydrate (1:1) → HCID 54358025, compound

HRID 1107811Notes

Reaction equation

HRID 1107811 reaction equation
O.[NH2:2][NH2:3].[CH:4]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH:15]=O)=[C:9]1[C:17]([O:19]C)=O)=[CH:5][CH2:6][CH3:7]>C(O)(=O)C.ClCCl>[CH2:4]([N:8]1[C:9]2[C:17](=[O:19])[NH:2][N:3]=[CH:15][C:10]=2[C:11]([CH3:14])=[C:12]1[CH3:13])[CH:5]=[CH:6][CH3:7]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 73472055HCID 73472055, compound

Product 1

HCID 54358025HCID 54358025, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

1.10 g (0.0220 mole) of hydrazine hydrate was added to a solution of 4.50 g (0.0191 mole) of methyl 1-butenyl-3-formyl-4,5-dimethylpyrrole-2-carboxylate (cis/trans=24/76) in 47 ml of acetic acid and the resulting mixture was stirred at 100° C. for 2 hours. The reaction mixture cooled to room temperature was poured into ice-water. Precipitated crystals were collected by filtration and washed with water. The crystals thus obtained were dissolved in 300 ml of dichloromethane and the solution was dried over anhydrous sodium sulfate. Distilling off the solvent gave 3.53 g (0.0163 mole) of 1-(2-butenyl)-2,3-dimethyl-6,7-dihydropyrrolo[2,3-d]-pyridazine-7-one (cis/trans=21/79) as pale brown crystals.

Workup

  1. temperatureThe reaction mixture cooled to room temperature
  2. customPrecipitated crystals
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customThe crystals thus obtained
  6. dry with materialthe solution was dried over anhydrous sodium sulfate
  7. distillationDistilling off the solvent

Sources & evidence

ORD record
ord-82961c13d05c43568f8fea901bd79aad
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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