Hydrazine hydrate (1:1) → HCID 178432363, compound

HRID 1107814Notes

Reaction equation

HRID 1107814 reaction equation
O.[NH2:2][NH2:3].[CH:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:7]=1[C:13]([O:15]C)=O)=O>C(O)(=O)C>[CH3:12][C:9]1[N:8]=[C:7]2[C:13](=[O:15])[NH:2][NH:3][CH:4]=[C:6]2[C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10773740Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 178432363HCID 178432363, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

1.50 g (0.030 mole) of hydrazine monohydrate were dropwised added slowly to a solution of 4.00 g (0.022 mole) of methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate in 80 ml of acetic acid at room temperature and the resulting mixture was stirred at 110° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into ice-water. The resulting precipitates were collected by filtration and washed well with water. The precipitates were dissolved in dichloromethane and the solution was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 3.40 g of 2,3-dimethyl-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one as a grayish-white powder.

Workup

  1. customAfter completion of the reaction
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed well with water
  5. dissolutionThe precipitates were dissolved in dichloromethane
  6. dry with materialthe solution was dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0627c6bfa5d74a669cb5789094cec425
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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