Methylhydrazine → 4-Chlorobenzaldehyde (N-methyl)hydrazone

HRID 1005275Notes

Reaction equation

HRID 1005275 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][NH:11][NH2:12]>C(O)C>[CH3:10][NH:11][N:12]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 77264-Chlorobenzaldehyde

Product 1

HCID 681484424-Chlorobenzaldehyde (N-methyl)hydrazoneYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

56.2 g (0.4 mol) of 4-chlorobenzaldehyde were added dropwise to a solution of 18.4 g (0.4 mol) of methylhydrazine in 100 ml of ethanol. The mixture was then refluxed for 4 hours. After cooling, the reaction mixture was concentrated. The residue was taken up in methyl tert-butyl ether. The ether phase was finally washed with water, dried over magnesium sulfate and then concentrated. Yield: 97%.

Workup

  1. temperatureThe mixture was then refluxed for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated
  4. washThe ether phase was finally washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6746dcfcb670405b8e49d72dd182ee67
Source dataset
uspto-grants-2000_04
Patent number
US06054412

Reaction notes

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