Sodium Bicarbonate → 4,6-Dichlorotryptophan

Participants

Reaction Steps

Dissolve ethyl 2-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate (1.10g, 3.65mmol ) in acetic acid (200mL) and add activated zinc dust (1.25g, 19.2mmol). Stir at room temperature for 72 hours. Evaporate the acetic acid in vacuo to give a white oil. Take the white oil up in ethyl acetate (200mL) and treat with saturated sodium hydrogen carbonate (500mL). Filter t he resulting white precipitate and separate the organic phase. Wash with saturated sodium hydrogen carbonate (100mL) a nd brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (1.02g, 98%).

Provenance & Evidence