Hydrochloric Acid → HCID 86681752, compound

Participants

Reaction Steps

A mixture of tert-butyl 2-(5-cyano-1,3-dioxoisoindolin-2-yl)acetate (0.440 g, 1.537 mmol), aqueous 1M HCl (0.768 ml, 0.768 mmol) and 10% w/w Pd/C (a catalytic amount) in MeOH (30 ml) was hydrogenated in a Parr apparatus at 40 psi for 4 hours. 37% HCl aqueous solution (0.0316 ml, 0.384 mmol) was added, and the mixture hydrogenated at 45 psi for additional 4 hours. The mixture was filtered, and the solution evaporated under vacuum. The crude was dissolved in MeOH (25 ml) and added to a suspension of new 10% w/w Pd/C (a catalytic amount) in MeOH (5 ml); 37% HCl (0.0316 ml, 0.384 mmol) was added at 0° C., and the mixture was hydrogenated at 45 psi 3 hours. The catalyst was filtered off, and the solution concentrated under vacuum. The crude was triturated with diethyl ether to afford tert-butyl 2-(5-(aminomethyl)-1,3-dioxoisoindolin-2-yl)acetate hydrochloride (0.409 g, 1.252 mmol, 81% yield, MS/ESI+ 291.1 [MH]+).

Provenance & Evidence