Water → 8-Methyl-3,4-diphenylcinnoline

HRID 643289Notes

Reaction equation

HRID 643289 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:8]=[N:9][C:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:11]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 866089501,2-Diphenylethane-1,2-dione (2-methylphenyl)-hydrazone

Product 1

HCID 118567038-Methyl-3,4-diphenylcinnolineYield 5.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1,2-Diphenylethane-1,2-dione (2-methylphenyl)-hydrazone (0.50 g, 1.59 mmol) was dissolved in 70% of sulfuric acid (10 mL) and the reaction was stirred at room temperature overnight. The reaction was poured into iced water and extracted with ethyl acetate. The combined organics was dried over MgSO4 and concentrated. The material was purified via column chromatography using 5-100% ethyl actetate in hexane as the eluent to yield 0.025 g of the title compound as an orange solid. MS (ESI) m/z 297([M+H]+); HRMS (ESI, [M+H]+) 297.1406.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics was dried over MgSO4
  3. concentrationconcentrated
  4. customThe material was purified via column chromatography

Sources & evidence

ORD record
ord-25bccea003be4a56baf96c772ab9bc1c
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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