p-Fluorobenzoylacetonitrile → HCID 55170688, compound

HRID 1775569Notes

Reaction equation

HRID 1775569 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=O)=[CH:4][CH:3]=1.Cl.[NH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH2:15]>C(O)C>[NH2:10][C:9]1[N:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:15]=[C:6]([C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 2783172p-FluorobenzoylacetonitrileHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 55170688HCID 55170688, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluorobenzoylacetonitrile (5 g, 30.7 mmol) and ethyl hydrazinoacetate hydrochloride (4.74 g, 30.7 mmol) in ethanol (50 mL) was heated to reflux for 2 h. The reaction mixture was concentrated in vacuo. The crude reaction mixture was partitioned between CH2Cl2 and concentrated aqueous ammonia. The aqueous phase was extracted with CH2Cl2 and the organic phases combined, dried over MgSO4, filtered and evaporated to give ethyl 2-(5-amino-3-(4-fluorophenyl)-1H-pyrazol-1-yl)acetate as a solid (7.4 g), which was used as such in the subsequent step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe crude reaction mixture
  5. customwas partitioned between CH2Cl2 and concentrated aqueous ammonia
  6. extractionThe aqueous phase was extracted with CH2Cl2
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-3cd4d42e6ece4cf6bdd1a05f40318f5c
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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