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. 2019 Aug 20;44(3):181–185. doi: 10.1584/jpestics.D19-028

Scheme 1.  Synthesis of cuminaldehyde derivatives. Reagents and conditions: (a) EtOH, 1 M NaOH, rt, 8 hr, 60–85%; (b) EtOH, NH2OH·HCl, NaOH, reflux, 8 hr, 49–67%; (c) acetic acid, N2H4·H2O, reflux, 4 hr, 60–80%. R=o-CH3(1a, 2a, 3a); o-Br(1b, 2b, 3b); o-Cl(1c, 2c, 3c); o-F(1d, 2d, 3d); m-CH3(1e, 2e, 3e); m-Br(1f, 2f, 3f); m-Cl(1g, 2g, 3g); m-F(1h, 2h, 3h); p-CH3(1i, 2i, 3i); p-Br(1j, 2j, 3j); p-Cl(1k, 2k, 3k); p-F(1l, 2l, 3l).

Scheme 1.  Synthesis of cuminaldehyde derivatives. Reagents and conditions: (a) EtOH, 1 M NaOH, rt, 8 hr, 60–85%; (b) EtOH, NH2OH·HCl, NaOH, reflux, 8 hr, 49–67%; (c) acetic acid, N2H4·H2O, reflux, 4 hr, 60–80%. R=o-CH3(1a, 2a, 3a); o-Br(1b, 2b, 3b); o-Cl(1c, 2c, 3c); o-F(1d, 2d, 3d); m-CH3(1e, 2e, 3e); m-Br(1f, 2f, 3f); m-Cl(1g, 2g, 3g); m-F(1h, 2h, 3h); p-CH3(1i, 2i, 3i); p-Br(1j, 2j, 3j); p-Cl(1k, 2k, 3k); p-F(1l, 2l, 3l).