Zhou Xin-rui
2005
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Journal
Fine Chemical Intermediates
Abstract
Condensation of 3-methoxybenzaldehyde with nitromethane at the temperature 20℃resulted in 3-methoxy-β-nitrostyrene with 88% of yield. Reduction with LiAlH4 in the solvent THF at room temperature afforded 3-methoxy-phenethylamine with 85.4% of yield that reacted with formaldehyde and 20% hydrochloric acid through Pictet-Spengler reaction under the temperature of 100℃ to form 6-methoxyterahydroisoquinoline, and its the yield was 80%. Then dehydrogenation in the presence of Raney Ni at 190℃ afforded 6-methoxyisoquinoline (yield 86.5%), and bromination with NBS in the presence of strong sulfate acid at the low temperature (-5℃) gave 6-methoxy-5-bromoisoquinoline (yield 93%). Finally, bomo-substituent cyanidation with cuprous cyanide in the presence of DMSO at 190℃ gave 6-mehoxyisoquinoline-5-carbonitrile (yield 95%) that was an important intermediate of drug and dye and characterized by IR, HNMR and MS.