Synthesis of 2,3- diphenylquinoxaline

BACKGROUND

2,3- diphenylquinoxaline

Aim:

To prepare 2,3- diphenylquinoxaline from benzyl.

Principle:

This is a method of condensation of an aryl 1,2-diamine with a 1,2-dicarbonyl compound by heating in a solvent like rectified sprit. Here condensation reaction of 1,2-diamines with α-diketones occurs with cyclization.¹ 

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Mechanism:

Use:

Used as anti-viral, anti-bacterial, anti-inflammatory, anti-protozoal, anti-cancer (colon cancer therapies), antidepressant, anti-HIV agent and as kinase inhibitor etc.

REQUIREMENTS

Chemicals:     

• o-Phenylenediamine
• Benzil
• Rectified sprit

Apparatus:     

• Beaker
• Buchner funnel
• Measuring cylinder
• Filter paper

PROCEDURE

To a warm solution of 2.1 g (0.01 mol) of benzil in 8 ml of rectified spirit, mix a solution of 1.1 g (0.01 mol) of o-phenylenediamine in 8 ml rectified spirit. Warm in a water bath for 30 min, add water until a slight cloudiness persists and allow to cool. Filter and recrystallise from aqueous ethanol to give 1.43 g (51%) of 2,3-diphenylquinoxaline, m.p. 125-126 °C.

Calculation

Here limiting reagent is benzil; hence yield should be calculated from its amount taken.

C₁₄H₁₀O₂ = Molecular formula of benzil

C₂₀H₁₄N₂ = Molecular formula of 2,3-diphenylquinoxaline

Molecular weight of benzil = 210 g/mole

Molecular weight of 2,3-diphenylquinoxaline = 282 g/mole

Theoretical yield

210 g benzil forms 282 g 2,3-diphenylquinoxaline

Therefore, 2.1 g benzil will form …….? (X) g 2,3-diphenylquinoxaline = 2.82 g

Theoretical yield = 2.82 g

Practical yield = ————- g

% Yield = (Practical Yield)/(Theoretical Yield) × 100

CONCLUSION

2,3-diphenylquinoxaline was synthesized and the percentage yield was found to be………..%

REFERENCES

1. Vogel’s Textbook of Practical Organic Chemistry by Brian S. Furniss, Antony J. Hannaford, Peter W. G. Smith & Austin R. Tatchell; Fifth Edition; Page No. 1190.

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