Methylhydrazine → HCID 178481733, compound

HRID 1726382Notes

Reaction equation

HRID 1726382 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])C.[CH3:16][NH:17][NH2:18]>CCO>[F:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]1[CH:5]=[C:4]([OH:3])[N:17]([CH3:16])[N:18]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 296342Ethyl 3-(2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 178481733HCID 178481733, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl-2-fluorobenzoylacetate (4.3 ml, 24 mmol) in EtOH (48 ml) was added methylhydrazine (1.32 ml, 25 mmol) under N2 at RT. The reaction was heated at reflux for 18 h. The mixture was then evaporated, and the off white solid residue taken up in hot EtOAc. The mixture was cooled down, and the white solid not dissolved was collected via filtration and washed with hexane, then dried under reduced pressure to yield 5-(2-fluorophenyl)-2-methyl-2H-pyrazol-3-ol (intermediate XXVIIIa, 3.54 g, 77% yield). M+=193.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. customThe mixture was then evaporated
  4. temperatureThe mixture was cooled down
  5. dissolutionthe white solid not dissolved
  6. filtrationwas collected via filtration
  7. washwashed with hexane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0a73edcd85f24dbd8254fd361cf78fc6
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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