Hydrochloric Acid → 1-[(2-Aminophenyl)methyl]-1-(4-chlorophenyl)hydrazine

HRID 1979683Notes

Reaction equation

HRID 1979683 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][N:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[NH2:12])([O-])=O.Cl>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][N:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[NH2:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 133765441-[(2-Nitrophenyl)methyl]-1-(4-chlorophenyl)hydrazine

Product 1

HCID 133765451-[(2-Aminophenyl)methyl]-1-(4-chlorophenyl)hydrazineYield 80%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6.5 g (0.023 m) of 1-[(2-nitrophenyl)methyl]-1-(4-chlorophenyl)hydrazine of Example 12a in 150 ml of 95% ethanol and 25 ml of water, 12.8 g (0.23 g-atom) of iron and 1 ml of concentrated HCl was added. The mixture was refluxed for 0.5 hours, cooled, Celite added and filtered. The filtrate was evaporated and the residual material was partitioned between 10% NaOH and ether. The ether extract was dried (Na2SO4), filtered and evaporated to afford a solid which was triturated with hexane and filtered giving 4.5 g (80%) of 1-[(2-aminophenyl)methyl]-1-(4-chlorophenyl)hydrazine, m.p. 83°-87° C.

Workup

  1. temperatureThe mixture was refluxed for 0.5 hours
  2. temperaturecooled
  3. additionCelite added
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residual material was partitioned between 10% NaOH and ether
  7. extractionThe ether extract
  8. dry with materialwas dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto afford a solid which
  12. customwas triturated with hexane
  13. filtrationfiltered

Sources & evidence

ORD record
ord-3d742b1a96d749448114b44a3ca56110
Source dataset
uspto-grants-1984_11
Patent number
US04482547

Reaction notes

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