Hydrochloric Acid → 1H-indole-7-carbohydrazide

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 2-(1H-indol-7-ylcarbonyl)hydrazinecarboxylate (I43) (0.202 g, 0.734 mmol) in 1,4-Dioxane (8 mL) was added 4M HCl in Dioxane (1.834 mL, 7.34 mmol) dropwise over 1 minutes. The solution was then allowed to stir at room temperature and under argon for 18 hours. Analysis by LCMS and TLC showed starting material to still be present, 4M HCl in Dioxane (5.50 mL, 22.01 mmol) was thus added and the solution was further stirred for 2 hours. TLC confirmed reaction completion and the solvent was evaporated in vacuo. The remaining solid was then azeotroped with ether (2×10 mL). The remaining solid was then loaded onto an SCX cartridge (5 g) and washed with methanol (2×20 mL) before being eluted with 2M NH3/MeOH. The solvent was then evaporated in vacuo and the remaining solid was dried in a vac-oven to yield the product in 0.113 g.

Provenance & Evidence