Hydrochloric Acid → 1H-indole-7-carbohydrazide

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.

1. additionwas thus added
2. stirringthe solution was further stirred for 2 hours
3. customreaction completion
4. customthe solvent was evaporated in vacuo
5. customThe remaining solid was then azeotroped with ether (2×10 mL)
6. washwashed with methanol (2×20 mL)
7. washbefore being eluted with 2M NH3/MeOH
8. customThe solvent was then evaporated in vacuo
9. customthe remaining solid was dried in a vac-oven
10. customto yield the product in 0.113 g

ORD record

ord-5fbbad4d4da949888efe8424aa08f7d8

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2