Water → 7-Bromo-1,2,3,4-tetrahydroquinoline

A solution of 7-bromoquinoline (J. Amer. Chem. Soc., 1947, 69, 705) (362 mg, 1.74 mmol) in glacial acetic acid (10 ml) was treated portion-wise with sodium cyanoborohydride (437 mg, 7.0 mmol) under argon at room temperature. After 18 h at this temperature, the mixture was cooled in an ice bath and to it was added water (35 ml) and 50% aq. sodium hydroxide until pH 14 was attained. The mixture was extracted with dichloromethane and the organic phase washed with saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo to a residue which was purified by column chromatography over silica gel eluting with a gradient of methanol/dichloromethane to give the title compound (D15) (168 mg, 46%). MH+ 212/214.

1. temperaturethe mixture was cooled in an ice bath and to it
2. extractionThe mixture was extracted with dichloromethane
3. washthe organic phase washed with saturated sodium chloride solution
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo to a residue which
6. customwas purified by column chromatography over silica gel eluting with a gradient of methanol/dichloromethane

ORD record

ord-6fe104b99dfa44298db07528b1b6922a

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06316450B1