Water → HCID 18676092, compound

HRID 1635514Notes

Reaction equation

HRID 1635514 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH:8]=[CH:9][N:10](C)C)=[CH:3][CH:2]=1.[ClH:14].[F:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1.O>C(O)C>[Cl:14][C:6]1[CH:5]=[C:4]([C:7]2[N:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)[N:10]=[CH:9][CH:8]=2)[CH:3]=[CH:2][N:1]=1

Participants

5

Reactant 3

HCID 962WaterHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-

Product 1

HCID 18676092HCID 18676092, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(4-pyridyl)-2-(dimethylaminomethylene)ethanone (2.1 g, 0.01 mol) and 4-fluorophenylhydrazine hydrochloride (1.63 g, 0.01 mol) in 50 mL of ethanol was added 1 mL of water. The reaction mixture was heated at reflux for 1.5 h. Solvent was removed and the residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 2.5 g (93% yield) of product as a yellow oil: Anal. Calcd. for C14H9ClFN3: C, 61.44; H, 3.31; N, 15.35. Found: C, 61.52; H, 3.27; N, 14.73.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 h
  3. customSolvent was removed
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Sources & evidence

ORD record
ord-768e107b4f984d8cad41b645d09d2129
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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