p-Fluorobenzoylacetonitrile → HCID 55170688, compound

HRID 1525434Notes

Reaction equation

HRID 1525434 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 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-9d5c98a8eed74665a3b13734705db204
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

Loading…