Hydrochloric Acid → {1H-pyrrolo[2,3-c]pyridin-5-yl}methanamine dihydrochloride

Participants

Reaction Steps

A suspension of 2-cyano-4-(2-dimethylaminoethenyl)-5-nitropyridine (3.8 g) and 10% palladium on carbon (3 g) in 6 M HCl (10 mL) and methanol (50 mL) was shaken on a Parr apparatus under hydrogen (55 psi). After 16 h the mixture was filtered through celite, washing with methanol, and was basified with ammonium hydroxide and evaporated in vacuo. The crude product was purified by flash column chromatography (80:19:1 chloroform/methanol/ammonium hydroxide) to give the title compound as the free base. The free base was dissolved in a minimum volume of methanol and 1 M HCl in ether (2 equivalents) was added and after dilution with ether the solids were collected by filtration to give the title compound as a tan solid:

Provenance & Evidence