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0 °C

An aqueous (5 mL) solution of sodium nitrite (540.9 mg, 7.839 mmol) was added to a solution of 3-chloroaniline in water (7 mL), concentrated hydrochloric acid (3 mL) and ethanol (7 mL) via dropping funnel. The reaction was allowed to stir at 0° C. for ten minutes. This solution was poured into a dropping funnel and ice was added. This was added dropwise to a solution of cinnamaldehyde tosyl hydrazone (2.3 g, 7.682 mmol) in pyridine (20 mL). This was allowed to stir overnight. An aqueous workup was done extracting with dichloromethane three times. The combined layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (20% EtOAc/hexanes) to yield the title compound as a light purple solid (433.6 mg, 19%). 1H NMR (CDCl3) δ (ppm): 8.21 (m, 1H), 8.09 (d of t, 1H), 7.89 (d, 1H), 7.61 (m, 2H), 7.49 (m, 5H), 7.24 (d, 1H).

1. additionThis solution was poured into a dropping funnel
2. additionice was added
3. stirringto stir overnight
4. extractionAn aqueous workup was done extracting with dichloromethane three times
5. washThe combined layers were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified by column chromatography (20% EtOAc/hexanes)