Boron tribromide → 7-(2-Hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one
Reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[CH2:22][C:21]2[N:20]=[CH:19][CH:18]=[C:17]([CH3:23])[C:16]=2[C:15](=[O:24])[CH2:14]1.C(=O)([O-])O.[Na+]>ClCCl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[CH2:22][C:21]2[N:20]=[CH:19][CH:18]=[C:17]([CH3:23])[C:16]=2[C:15](=[O:24])[CH2:14]1Participants
Procedure
To a solution of boron tribromide (0.96 g) in dichloromethane (30 ml) was added dropwise at −78° C. a solution of 7-(2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.33 g) in dichloromethane (1 ml), and the mixture was gradually warmed to room temperature and stirred at room temperature for 1.5 hours. To the mixture were added carefully ice and sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 7-(2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.23 g).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
Sources & evidence
- ORD record
- ord-58402537833b4e61a0553bf54a9dff0c
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350749B1
Reaction notes
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