Water → 1,2-Diphenylethane-1,2-dione (2-methylphenyl)-hydrazone

HRID 643288

Reaction equation

HRID 643288 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[C:11]1([C:17](=O)[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(O)(=O)C>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][N:10]=[C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 8651BenzilHCID 71554o-Tolylhydrazinium(1+) chloride

Product 1

HCID 866089501,2-Diphenylethane-1,2-dione (2-methylphenyl)-hydrazoneYield 101.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-methylphenyl hydrazine hydrochloride (0.79 g, 5.0 mmol) and 1,2-diphenyl-ethane-1,2-dione (1.05 g, 5 mmol) in 20 mL of glacial acetic acid was refluxed for 30 min. The reaction was poured into water and extracted with ethyl acetate. The combined organics was dried over MgSO4 and concentrated to give 1.6 gram of 1,2-diphenylethane-1,2-dione (2-methylphenyl)-hydrazone as an orange solid. MS (ESI) m/z 315 ([M+H]+);

Workup

  1. temperaturewas refluxed for 30 min
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a58b27c657646648bfad80242fd5e7e
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Linked notes

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