Methanol → HCID 70491208, compound

HRID 463544Notes

Reaction equation

HRID 463544 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6]C)=[C:4]([N+:10]([O-])=O)[CH:3]=1.NN.[CH3:15]O>[Ni]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH3:15])([NH2:6])[CH:4]([NH2:10])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 27368364-chloro-N-methyl-2-nitroaniline

Product 1

HCID 70491208HCID 70491208, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

32.5 g (0.175M) of 4-Chloro-2-nitro-N-methylaniline of A above are added gradually to 24 g Raney-Nickel (wet) and 48 g hydrazine in methanol. A large amount of heat is generated. After the addition is complete, the solution is heated to reflux for 3 hours and filtered to remove the metal catalyst. The solvent is removed and the residue dissolved in methylene chloride. The methylene chloride solution is extracted with water and the mixture is filtered to remove the emulsion. The layers are separated and the methylene chloride layer is dried over anhydrous magnesium sulfate. After removal of the solvent, the residue is recrystallized from hexane. The substituted phenylenediamine weighs 22.6 g (84% yield) and has a melting point of 51°-2° C.

Workup

  1. temperatureA large amount of heat
  2. additionAfter the addition
  3. temperaturethe solution is heated
  4. temperatureto reflux for 3 hours
  5. filtrationfiltered
  6. customto remove the metal catalyst
  7. customThe solvent is removed
  8. dissolutionthe residue dissolved in methylene chloride
  9. extractionThe methylene chloride solution is extracted with water
  10. filtrationthe mixture is filtered
  11. customto remove the emulsion
  12. customThe layers are separated
  13. dry with materialthe methylene chloride layer is dried over anhydrous magnesium sulfate
  14. customAfter removal of the solvent
  15. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-53b572a1796d4a96928b78df2d499802
Source dataset
uspto-grants-1985_05
Patent number
US04520196

Reaction notes

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