Ethanol → HCID 86152363, compound

HRID 1493707Notes

Reaction equation

HRID 1493707 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([CH2:9][CH2:10][CH2:11][CH3:12])=O)=[CH:3][CH:2]=1.[CH:13]([NH:15][NH2:16])=[O:14].C1COCC1.C(O)C>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[N:16][NH:15][CH:13]=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 12229HydrazinecarboxaldehydeHCID 743441-Pentanone, 1-(4-pyridyl)-

Product 1

HCID 86152363HCID 86152363, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 14.26 gm (0.0956 mole) of n-butyl 4-pyridyl ketone, 5.70 gm (0.0956 mole) of formylhydrazine, 50 ml of THF, 30 ml of absolute ethanol and 0.1 gm of p-toluenesulfonic acid is refluxed 24 hr. The reaction is chilled to give a white solid which is collected and discarded. The filtrate is concentrated in vacuo to furnish a solid. This material is dissolved in methylene chloride. The methylene chloride solution is washed with saturated sodium bicarbonate solution; then brine. The organic layer is dried over magnesium sulfate and concentrated in vacuo in the presence of excess hexane to yield 5.14 gm (26%) of the title compound having a melting point of 143.4° C.

Workup

  1. temperatureThe reaction is chilled
  2. customto give a white solid which
  3. customis collected
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto furnish a solid
  6. washThe methylene chloride solution is washed with saturated sodium bicarbonate solution
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. concentrationconcentrated in vacuo in the presence of excess hexane

Sources & evidence

ORD record
ord-8ef0abd63a154b39a198e956bde8d011
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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