Sodium Carbonate → HCID 68132942, compound

Participants

Reaction Steps

55 G. of rac.-α-{[(3-methoxybenzyl)amino]methyl}-3-nitrobenzyl alcohol hydrochloride and 165 g. of polyphosphoric acid (84.1% P2O5) are heated to 100° for 45 minutes. After the addition of a little ice and ethyl acetate the mixture is made alkaline with sodium carbonate and extracted. The ethyl acetate extract (46 g.) is chromatographed on 3.7 kg. of silica gel. With ether-acetone-diethylamine 19:1:1 there are eluted two uniform main fractions of 7.0 g. and 22.2 g. After acidification with ethanolic hydrochloric acid, crystallization and recrystallization from methanol-ether, from the first fraction there is obtained rac.-1,2,3,4-tetrahydro-5-methoxy-4-(3-nitrophenyl)isoquinoline hydrochloride, m.p. 217°-219° and from the second rac.-1,2,3,4-tetrahydro-7-methoxy-4-(3-nitrophenyl)isoquinoline hydrochloride, m.p. 253°-255°.

Provenance & Evidence