Phenacylamine → 2-Aminoacetophenone 4-chlorophenylhydrazone

HRID 373831Notes

Reaction equation

HRID 373831 reaction equation
[NH2:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1>CCO.CC(O)=O.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][N:19]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2][NH2:1])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 11952PhenacylamineHCID 70624(4-Chlorophenyl)hydrazine

Product 1

HCID 867463512-Aminoacetophenone 4-chlorophenylhydrazoneYield 84%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 10.43 g 2-aminoacetophenone and 11.0 g 4-chlorophenylhydrazine in 30 ml EtOH and 10 ml HOAc was refluxed for one hour. The cooled reaction mixture was diluted with water and the precipitate was collected, washed with water, and dried to give 16.83 g solid. Recrystallization from methanol gave 3.48 g solid, m.p. 109°-112° C.

Workup

  1. temperaturewas refluxed for one hour
  2. customThe cooled reaction mixture
  3. customthe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1b4ee9bfccff4cda888a1d14c2e6eaff
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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