Water → HCID 69331922, compound

HRID 915011Notes

Reaction equation

HRID 915011 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH2:19][CH3:20].O>CN(C=O)C.CCOC(C)=O.CCCCCC>[CH2:19]([N:13]1[C:12](=[O:15])[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:14]1)[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 59980711HCID 59980711, compound

Product 1

HCID 69331922HCID 69331922, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

Under nitrogen atmosphere, 6-(phenylethynyl)-3(2H)-pyridazinone (15.54 g) was added to a suspension of NaH (60% in oil suspension) (3.33 g) in DMF (90 ml) and the mixture was stirred at 50-55° C. for 30 minutes. Under ice-cooling, iodoethane (6.97 ml) was added to the mixture and the mixture was stirred at 50-55° C. for 3 hours. After addition of water, the reaction mixture was extracted with EtOAc, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v) to give 2-ethyl-6-(phenylethynyl)-3(2H)-pyridazinone as a solid (14.06 g).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 50-55° C. for 3 hours
  3. extractionthe reaction mixture was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue

Sources & evidence

ORD record
ord-92cc1b20fc80428facae2136472f96bf
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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