Hydrochloric Acid → 191041-29-9

To 7-nitro-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid methyl ester (5.0 g, 21.2 mmol) in dry tetrahydrofuran (18.5 ml) was added 10M borane-methyl sulfide complex (2.4 ml). The mixture was heated at reflux for 1.5 h while distilling off the methyl sulfide formed. The reaction mixture was cooled and methanol (2.7 ml) was added cautiously followed by 6N hydrochloric acid (5.4 ml). The mixture was then refluxed for 2.5 h and concentrated to dryness under reduced pressure. The solid residue was dissolved in water, the solution basified with 2.5N sodium hydroxide solution and the product extracted into dichloromethane. The crude product was purified by chromatography using silica gel and 5% methanol saturated with ammonia in dichloromethane to yield 7-nitro-1,2,3,4-tetrahydroisoquinoline-3-methanol (1.71 g).

1. temperatureThe mixture was heated
2. temperatureat reflux for 1.5 h
3. distillationwhile distilling off the methyl sulfide
4. customformed
5. temperatureThe reaction mixture was cooled
6. temperatureThe mixture was then refluxed for 2.5 h
7. concentrationconcentrated to dryness under reduced pressure
8. dissolutionThe solid residue was dissolved in water
9. extractionthe product extracted into dichloromethane
10. customThe crude product was purified by chromatography

ORD record

ord-54a79d0c03a64cc7b733abb3c7b66731

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140322