Methylhydrazine → HCID 62880533, compound

HRID 2359965Notes

Reaction equation

HRID 2359965 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[CH2:4][C:5](=[O:6])[N:13]([CH3:12])[N:14]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 62880533HCID 62880533, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Ethyl 4,4-difluoroacetoacetate (30.12 g, 0.172 mol) was stirred in toluene (600 mL) over ice water. Solution of N-methylhydrazine (7.6 mL, 0.14 mol) in toluene (200 mL) was added slowly, dropwise over 20 min. The reaction mixture was heated at 100° C. for 2 hours. The reaction mixture evaporated to dryness. The resulting material was triturated with methyl t-butylether/heptane to give 3-(difluoromethyl)-1-methyl-1H-pyrazol-5(4H)-one in three batches (total 10.7 g, 51%) as orange powder. This material was used without further purification for the next reaction. Step 2:

Workup

  1. customThe reaction mixture evaporated to dryness
  2. customThe resulting material was triturated with methyl t-butylether/heptane

Sources & evidence

ORD record
ord-cd7e26c2d02242a882b8820c48babb20
Source dataset
uspto-grants-2014_04
Patent number
US08686018B2

Reaction notes

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