Methylhydrazine → HCID 178481857, compound

HRID 2090532Notes

Reaction equation

HRID 2090532 reaction equation
[F:1][CH:2]([F:11])[C:3](=O)[CH2:4][C:5](OCC)=[O:6].[CH3:12][NH:13][NH2:14]>C1(C)C=CC=CC=1>[F:1][CH:2]([F:11])[C:3]1[CH:4]=[C:5]([OH:6])[N:13]([CH3:12])[N:14]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 178481857HCID 178481857, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 208.6 g (1257 mmol) of ethyl 4,4-difluoro-3-oxobutanoate (VII-1) in 1000 ml of toluene was added 57.8 g (1257 mmol) of methylhydrazine by dropwise addition with cooling. After 90 min under reflux the reaction mixture was cooled down and concentrated. After 1500 ml of diethyl ether had been added, the reaction mixture was stirred and the insoluble material was filtered off. The filtrate was concentrated to obtain 137.5 g (74% of theory) of 3-(difluoromethyl)-1-methyl-1H-pyrazol-5-ol (IX-1) as a reddish orange solid which was used in the next reaction step without further purification.

Workup

  1. additionby dropwise addition
  2. temperaturewith cooling
  3. temperatureAfter 90 min under reflux the reaction mixture
  4. temperaturewas cooled down
  5. concentrationconcentrated
  6. additionAfter 1500 ml of diethyl ether had been added
  7. filtrationthe insoluble material was filtered off
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d9b02768842f4db48dea71354a0dcf7d
Source dataset
uspto-grants-2013_05
Patent number
US08436191B2

Reaction notes

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