Acetophenone → Acetophenone benzoylhydrazone

HRID 1077671Notes

Reaction equation

HRID 1077671 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12]>O1CCCC1.Cl>[C:1]([NH:9][N:10]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7410AcetophenoneHCID 11955Benzoylhydrazine

Product 1

HCID 346107Acetophenone benzoylhydrazone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of benzoic acid hydrazide (5.70 g, 0.042 mol) in tetrahydrofuran (75 mL) was added acetophenone (5.5 g, 0.046 mol) followed by concentrated HCl (3 drops). The reaction was allowed to stir for 12 h at 25° C. during which time the product precipitated as a colorless crystalline solid. The product was filtered, washed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL), and the crystalline solids were dried in vacuo (6.65 g, 64%). 1H NMR (CD2Cl2): δ2.35 (s, 3H, CH3), 7.30-8.0 (m, 10H, Ph), 9.0 (br, 1H, NH). All other substrates were prepared in a similar fashion.

Workup

  1. customprecipitated as a colorless crystalline solid
  2. filtrationThe product was filtered
  3. washwashed with tetrahydrofuran (1×30 mL), diethyl ether (3×60 mL) and pentane (2×60 mL)
  4. customthe crystalline solids were dried in vacuo (6.65 g, 64%)
  5. customAll other substrates were prepared in a similar fashion

Sources & evidence

ORD record
ord-41b732a171814d6d92461c9464786cfc
Source dataset
uspto-grants-1996_08
Patent number
US05543571

Reaction notes

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