A solution of 6.7 g KOH in 100 mL H2O, under an inert atmosphere and magnetically stirred, was brought to 75 °C, and 10 g ergotamine tartrate (ET) added. The reaction mixture turned yellow as the ergotamine went into solution over the course of 1 h. The stirring was continued for an additional 3 h. The reaction mixture was cooled to about 10 °C with an external ice bath, and acidified to a pH of about 3.0 by the dropwise addition of 2.5 N H2SO4. White solids started to appear early in the neutralization; approximately 60 mL of sulfuric acid was required.
i'm somewhat confused by the above procedure...
Shouldn't adding ET to a basic solution form ergotamine freebase? If so, then why was a precipitate formed when the acid was added? Or does ET not act like a good alkaloid should? Also, i'm guessing that the acidification casues the below reaction...
does:
RCONH2 + H+ + H2O ---> RCOOH + NH4
and
RCONH2 + OH- + H20 ---> RCOO- + NH3 + H20
apply to LSA? I would imagine it would, but i have very little formal background in chemistry, so maybe i'm missing something...
- nevry.
p.s. if the above reactions apply to LSA, then shouldn't an a/b extraction convert LSA to Lysergic acid???
- nevry.