Carbostyril, 3,4-dihydro-7-fluoro- → 7-Fluoro-1,2,3,4-tetrahydroquinoline
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=O)[NH:9]2)=[CH:4][CH:3]=1>O1CCCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 7-fluoro-1,2,3,4-tetrahydroquinolin-2-one (1.5 g, 9.08 mmol) in tetrahydrofuran (50 ml) was dropwise BH3 in THF (1M, 90 ml), the solution was stirred for 24 h at 60° C. The reaction mixture was cooled and then quenched by the addition of methanol (15 ml) and HCl (conc) (5 ml), then stirred for 1 h at 60° C. The reaction mixture was cooled to room temperature and adjusted to pH 12 with sodium hydroxide (4 mol/L), extracted with (3×15 ml) of ethyl acetate and the organic layers were combined and dried over anhydrous magnesium sulfate, concentrated in vacuo to give a residue, which was purified by a silica gel column chromatography with 3% ethyl acetate in petroleum ether to afford 7-fluoro-1,2,3,4-tetrahydroquinoline as a yellow solid (0.9 g, 66%).