Hydrochloric Acid → HCID 68937404, compound

Participants

Reaction Conditions

Reaction Steps

0.22 g of palladium on charcoal (10 wt. %) and 3.74 g (59.25 mmol) of ammonium formate are added to 3.57 g (11.65 mmol) of 8-nitro-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 66) suspended in 80 mL of anhydrous dimethylformamide. The reaction mixture is stirred overnight at 60° C. then 0.50 g of palladium on charcoal (10 wt. %) and 0.75 g (11.89 mmol) of ammonium formate are added. Stirring is continued for 4 h. The mixture is then diluted in ethyl acetate and filtered on celite. The filtrate is evaporated and triturated in ether to give, after filtration, 3.16 g of a mixture of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 8-formylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate. The beige residue is suspended in 40 mL of anhydrous ethanol before adding 11.7 mL (23.29 mmol) of 2M hydrochloric acid in diethyl ether. The solution is stirred for 90 minutes then filtered to give 3.34 g (92%) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride in the form of a light violet solid.

Provenance & Evidence