Toluene → Acetylpyridine diphenylhydrazone

HRID 1084477Notes

Reaction equation

HRID 1084477 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)(=O)[CH3:9].Cl.[C:18]1([NH:24][NH:25]C2C=CC=CC=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>O.CCCCCC>[C:18]1([N:24]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:25]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH3:9])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 142862-AcetylpyridineHCID 517045Sodium AcetateHCID 122347261,2-Diphenylhydrazine hydrochloride

Product 1

HCID 54461296Acetylpyridine diphenylhydrazone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8058HexaneSolvent

Procedure

A mixture of 120 ml toluene, 80 ml hexane, 24.2 g acetylpyridine, 24.2 g of diphenylhydrazine hydrochloride, and 30 g of anhydrous sodium acetate was stirred and heated at reflux in a flask equipped with a water separator until no more water was being collected (about 2 hours). The reaction mixture was filtered, and the filtrate was distilled under aspirator vacuum at 60° C. The residue was stirred with 100 ml of methanol with cooling to keep temprature between -10° and -20° C. The resulting solid was collected, washed with 100 ml of cold methanol, and was dried in vacuo to give 43 g of acetylpyridine diphenylhydrazone, mp 84° C. λmax in methanol is 358 nm; absorptivity is 6.7×103.

Workup

  1. temperatureheated
  2. temperatureat reflux in a flask
  3. customwas being collected (about 2 hours)
  4. filtrationThe reaction mixture was filtered
  5. distillationthe filtrate was distilled under aspirator vacuum at 60° C
  6. stirringThe residue was stirred with 100 ml of methanol
  7. temperaturewith cooling
  8. customto keep temprature between -10° and -20° C
  9. customThe resulting solid was collected
  10. washwashed with 100 ml of cold methanol
  11. customwas dried in vacuo

Sources & evidence

ORD record
ord-2786021bae0d44c99de96365eb9977cd
Source dataset
uspto-grants-1991_04
Patent number
US05004812

Reaction notes

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