反应详情

温度

50 °C

6-Benzyl-3-nitro-5,6,7,8-tetrahydro-[1,6]-naphthyridine (790 mg; 2.93 mmol) was dissolved in ethanol (100 ml), the solution heated at 50° C. and treated with a solution of stannous chloride dihydrate (2.65 g; 11.73 mmol) in conc. hydrochloric acid (10 ml). After 10 min, the reaction mixture was concentrated under reduced pressure, neutralised by addition of 2M aqueous sodium hydroxide and extracted with DCM. The extracts were combined, washed with water, saturated brine, dried (MgSO4) and evaporated to dryness in vacuo. The brown residue was dissolved in methanol and SiO2 added. The volatiles were removed under reduced pressure and the dried SiO2 placed on the top of a silica column and subjected to chromatography, eluting with ethanol in ethyl acetate (020%) ethanol gradient. The title compound was obtained as a white powder (275 mg; 39%).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionneutralised by addition of 2M aqueous sodium hydroxide
3. extractionextracted with DCM
4. washwashed with water, saturated brine
5. dry with materialdried (MgSO4)
6. customevaporated to dryness in vacuo
7. dissolutionThe brown residue was dissolved in methanol
8. additionSiO2 added
9. customThe volatiles were removed under reduced pressure
10. washeluting with ethanol in ethyl acetate (020%) ethanol gradient