Dimethylformamide → 1-Phenyl-4-pyridin-4-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 1867613Notes

Reaction equation

HRID 1867613 reaction equation
[C:1]1([NH:7][NH:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Ca+2].[H-].[CH3:21]N(C)C=O>>[C:1]1([N:7]2[CH:21]=[C:10]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)[C:9](=[O:17])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 3033859Calcium hydrideHCID 68566518N'-phenyl-2-pyridin-4-ylacetohydrazide

Product 1

HCID 685657321-Phenyl-4-pyridin-4-yl-1,2-dihydro-3H-pyrazol-3-one

Conditions

Temperature
170 °C

Procedure

N′-Phenyl-2-pyridin-4-ylacetohydrazide (460 mg, 2.02 mmol) and calcium hydride (141 mg, 3.34 mmol) were dissolved in dimethylformamide (8 mL) and heated at 170° C. After 8 h, the reaction cooled to ambient temperature and was filtered. The mixture was concentrated and redissolved in dichloromethane (50 mL). The precipitate was filtered and dried under high vacuum overnight to give the desired product. MS 238.04 (M+1)

Workup

  1. temperaturethe reaction cooled to ambient temperature
  2. filtrationwas filtered
  3. concentrationThe mixture was concentrated
  4. dissolutionredissolved in dichloromethane (50 mL)
  5. filtrationThe precipitate was filtered
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-a85efc9bfcc4478b836216ff1275ae5d
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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