Phenylhydrazine → HCID 18675458, compound

HRID 1635032Notes

Reaction equation

HRID 1635032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]=O)[CH:5]=[CH:6][CH:7]=1.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:17][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 115791652-(3-chlorophenyl)acetaldehyde

Product 1

HCID 18675458HCID 18675458, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-chlorophenyl)-acetaldehyde (5.80 g, 37.5 mmol) and phenylhydrazine (6.22 g, 57.5 mmol) in glacial acetic acid (150 mL) was saturated with nitrogen by bubbling N2 through the solution. The solution was then refluxed for about 2.5 hours. Solvent was removed in vacuo and the residue obtained was dissolved in DCM and washed with 1N HCl aqueous solution (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluting with EtOAc/hexane 1:6. The title compound was obtained as a reddish oil. Yield: 5.30 g, 62%. Rf=0.26 (silica, EtOAc/hexane 1:4)

Workup

  1. customby bubbling N2 through the solution
  2. temperatureThe solution was then refluxed for about 2.5 hours
  3. customSolvent was removed in vacuo
  4. customthe residue obtained
  5. washwashed with 1N HCl aqueous solution (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography on silica
  10. washeluting with EtOAc/hexane 1:6

Sources & evidence

ORD record
ord-5c7c4c4495d44f8ca21d9a26d4817e2f
Source dataset
uspto-grants-2003_01
Patent number
US06509336B1

Reaction notes

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