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Flash content link:

https://vlab.amrita.edu/repo/CHE/ORG/Alkylation_of_isatin/index.swf

Procedure:

1. To a solution of isatin (500 mg, 3.39 mmol) in dry DMF (10 mL ) was added powdered calcium hydride (472 mg, 11.21 mmol) and the mixture was stirred with gentle warming (40-50°C) for half an hour.

2. The allylating agent (16.99 mmol) was added to the reaction mixture at room temperature and was stirred for 4-5 h.

3. The reaction mixture was then poured slowly to a neutralized solution of brine.

4. The organic layer was extracted using ethyl acetate several times.

5. Evaporation of the solvent left a residue which was then subjected to chromatography on a silica gel column using 80:20 hexane ethyl acetate solvent mixture to afford the N-allyl derivative of isatin.