Hydrazine hydrate (1:1) → 5-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-3-amine

HRID 1507466Notes

Reaction equation

HRID 1507466 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=O)[CH2:11][C:12]#[N:13].O.[NH2:16][NH2:17]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[NH:17][N:16]=[C:12]([NH2:13])[CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 534039523-(2-Fluoro-4-methoxyphenyl)-3-oxopropanenitrile

Product 1

HCID 534182315-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-3-amineYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-(2-Fluoro-4-methoxyphenyl)-3-oxopropanenitrile (9.55 g, 49.4 mmol) suspended in ethanol (165 mL) was added hydrazine hydrate (1.743 g, 54.38 mmol). The resulting mixture was heated at reflux overnight. Then, the organic solvent was evaporated in vacuo and the resulting residue was chromatographed (eluting with 9:1 methylene chloride:methanol) to give 9.07 g (88% yield) of the title compound. LCMS (ESI): calc.=207; obs. M+H=208.2.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThen, the organic solvent was evaporated in vacuo
  4. customthe resulting residue was chromatographed
  5. wash(eluting with 9:1 methylene chloride:methanol)

Sources & evidence

ORD record
ord-5bee5a0291ef4ecab614cbe5b668ce95
Source dataset
uspto-grants-2015_12
Patent number
US09221814B2

Reaction notes

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