Acetic Acid → HCID 202258, compound

HRID 1483812Notes

Reaction equation

HRID 1483812 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)[C:5]#[N:6].O.[NH2:19]N.C(O)(=O)C>C(O)C>[F:14][C:13]([F:16])([F:15])[C:9]1[CH:8]=[C:7]([C:4]2[CH:3]=[N:2][NH:6][C:5]=2[NH2:19])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)2×HCID 3790410HCID 3790410, compound

Product 1

HCID 202258HCID 202258, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenyl)acrylonitrile (2.93 g, 12.20 mmol) in ethanol (35 ml) was added hydrazine hydrate (3.80 ml, 122 mmol) and acetic acid (6.98 ml, 122 mmol). Upon to reflux; a solution formed. After 5 hours, 0.25 mL of hydrazine hydrate was added and the reaction refluxed an additional 15 hours. The volatiles were removed in vacuo, and the residue partitioned between EtOAc and water. After extracting three times with EtOAc, the combined organics were washed twice with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated in vacuo to cleanly give 4-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine (2.7 g, 97% yield) as a light yellow oil.

Workup

  1. temperatureUpon to reflux
  2. customa solution formed
  3. temperaturethe reaction refluxed an additional 15 hours
  4. customThe volatiles were removed in vacuo
  5. customthe residue partitioned between EtOAc and water
  6. extractionAfter extracting three times with EtOAc
  7. washthe combined organics were washed twice with saturated aqueous NaHCO3
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-78f36c92f5324504909db9b49d1166d9
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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