Synthesis of 2-phenylindole from phenyl hydrazine

BACKGROUND

Principle:
Ayrl hydrazones are formed from a condensation reaction of an arylhydrazine and an aldehyde or ketone. Here phenylhydrazine condenses with acetophenone to produce acetophenone phenylhydrazone. Finally by Fischer indole synthesis the arylhydrazone (acetophenone phenylhydrazone) converts into the indole (2-phenylindole) in the presence of an acid catalyst.1

Aim: To prepare 2-phenylindole from phenyl hydrazine.

Reaction:


Mechanism:

Step 1:


Step 2:


Use:
2-Phenylindole is a reactant for preparation of organic light emitting diodes (OLEDs), anti-inflammatory agents, antibacterial, antifungal agents and fluorescent probes. It is a reactant in difluorohydroxylation reactions and Mannich-type reactions.

REQUIREMENTS

Chemicals:     Acetophenone

Phenylhydrazine

Glacial acetic acid

Dilute hydrochloric acid

Ethanol

Polyphosphoric acid

Calcium chloride etc.

Apparatus:     Round bottomed flask 500 ml

Reflux condenser

Thermometer

Beaker

Buchner funnel

Measuring cylinder

Filter paper etc.

PROCEDURE

Prepare acetophenone phenylhydrazone by boiling a mixture of 20 g (0.167 mol) of acetophenone and 18 g (0.167 mol) of phenylhydrazine carefully with ethanol 60 ml and a few drops of glacial acetic acid. Filter the cold reaction mixture, wash the solid with dilute hydrochloric acid followed by about 12 ml of cold rectified spirit. Recrystallise a small portion from ethanol and thus obtain a sample of pure acetophenone phenylhydrazone as a white solid, m.p. 106 °C. Place 28 g of the crude phenylhydrazone in a 250 ml beaker containing 180 g of polyphosphoric acid. Heat on a boiling water bath, stir with a thermometer and maintain at 100-120 °C for 10 min (the reaction is exothermic). Add 450 ml of cold water and stir well to complete solution of the polyphosphoric acid. Filter at the pump and wash well with water. Boil the crude solid under the reflux along with 300 ml of rectified spirit, add a little decolourising charcoal and filter through a preheated Buchner funnel. Wash the residue with 40 ml of hot rectified spirit. Cool the combined filtrates to room temperature, filter off the 2-phenylindole and wash it three times with 10 ml portions of cold alcohol. Dry in a vacuum desiccator over anhydrous calcium chloride. The yield of pure 2-phenylindole, m.p. 188-189 °C, is 20g (79%).

Calculation:

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

Molecular formula of phenylhydrazine = C6H8N2

Molecular formula of 2-phenylindole = C14H11N

Molecular weight of phenylhydrazine = 108 g/mole

Molecular weight of 2-phenylindole = 193 g/mole

Theoretical yield:

108 g phenylhydrazine forms 193 g 2-phenylindole

Therefore, 18 g phenylhydrazine will form …….? (X) g 2-phenylindole

= 32.16 g

Theoretical yield = 32.16 g

Practical yield = ————- g

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

CONCLUSION

2-phenylindole 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. 1161.
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