Methylhydrazine → HCID 178481859, compound

HRID 1939860Notes

Reaction equation

HRID 1939860 reaction equation
[CH3:1][NH:2][NH2:3].[F:4][C:5]([F:15])([F:14])[C:6](=O)[CH2:7][C:8](OCC)=[O:9]>C1(C)C=CC=CC=1>[OH:9][C:8]1[N:2]([CH3:1])[N:3]=[C:6]([C:5]([F:15])([F:14])[F:4])[CH:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178481859HCID 178481859, compoundYield 73,930.797%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl hydrazine (13.3 ml, 11.5 g, 0.25 mol) was added dropwise to a chilled (ice-bath) solution of ethyl 4,4,4-trifluoroacetoacetate (46.0 g, 0.25 mmol) in toluene (250 ml) at such a rate that the temperature of the reaction could be maintained below 10° C. (ice-bath cooling). Once the addition was complete the ice-bath was removed and stirring continued at room temperature for 1 hour and then at reflux (Dean-Stark) for 3 h. The mixture was allowed to cool to room temperature and allowed to stand over 3 days. The precipitate was collected by filtration and washed with hexane to give 5-hydroxy-1-methyl-3-trifluoromethylpyrazole (30.7 g) as a colorless solid, m.p. 170°-173° C.

Workup

  1. customthat the temperature of the reaction
  2. temperaturecould be maintained below 10° C.
  3. temperature(ice-bath cooling)
  4. additionOnce the addition
  5. customwas removed
  6. temperatureat reflux (Dean-Stark) for 3 h
  7. waitto stand over 3 days
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-510e0ee74a9342b0acf21d0813e63137
Source dataset
uspto-grants-1997_12
Patent number
US05698495

Reaction notes

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