Sulfuric Acid → HCID 23047464, compound

Participants

Reaction Steps

A suspension of 2-phenyl-2-[N-(2,2-dimethoxyethyl)-2-methylpropanamido]acetic acid (32.1 g) and methyl 4-fluorophenylpropiolate (22.5 g) in acetic anhydride (120 ml) was treated with triethylamine (16 ml) and the resulting amber solution was stirred at room temperature under argon for 24 hours. The solution was then added, dropwise during 10 minutes, to concentrated sulphuric acid (200 ml), stirring and cooling by means of an icebath. The mixture was stirred for 30 minutes and then it was poured into iced water (2.5 liters), and extracted with dichloromethane (3×400 ml). The combined extracts were washed with water (250 ml) and with brine (250 ml), dried over magnesium sulphate and evaporated, to give a brown solid, which was recrystallised from methanol, to give methyl 1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]isoquinoline-2-carboxylate in the form of an off-white solid, m.p. 170°-173° C.

Provenance & Evidence