Improved Efficient Conversion of Aldehydes to Nitriles via Their N, N-Dimethyl Hydrazones

References

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• General procedure (Method A): To a solution of hydrazone 2 (5 mmol) in CH3CN (15 ml) was added DMS (0.477 ml, 5 mmol) and K2CO3 (0.64 g, 5 mmol). This reaction mixture was monitored by TLC (EtOAc-hexane, 3:7). On completion of the reaction, the solid was filtered and the filtrate evaporated in reduced pressure. The resulting crude product was purified by column chromatography (silica, EtOAc-hexane, 2:8) to give pure compound 3. General procedure (Method B): To a solution of aldehyde 1 (5 mmol) in MeOH (25 ml) was added N,N-dimethylhydrazine (0.53ml.7 mmol). The reaction mixture is stirred at room temperature for (5–15 min) monitored by TLC. The solvent is then removed under reduced pressure. The residue obtained dissolved in CH3CN (15 ml) to which was added DMS (0.477 ml, 5 mmol) and K2CO3 (0.64 g, 5 mmol). This reaction mixture was refluxed for (8–10h). On completion of the reaction, the reaction was worked-up and purified as described in Method A
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