Sodium Hydroxide → 4-Allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline
Reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10](O)[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:16])[CH:2]=[CH2:3].P(Br)(Br)[Br:18].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([Br:18])[C:9]=2[N:8]=[CH:7][C:6]=1[CH3:16])[CH:2]=[CH2:3]Participants
Procedure
3.5 Grams of 4-allyloxy-8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline was dissolved in 40 ml of chloroform, to this solution was added dropwise a solution consisting of 2.8 g of phosphorus tribromide and 5 ml of chloroform under ice-cooled condition. The reaction mixture was stirred under ice-cooled condition for 2 hours, further stirred at room temperature for 2 hours. The reaction mixture was poured into a cold sodium hydroxide aqueous solution, then extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation, then the residue thus obtained was purified by a silica gel column chromatography (eluent: methylene chloride/methanol=100/1) to obtain 1.3 g of 4-allyloxy-8-bromo-3-methyl-5,6,7,8-tetrahydroquinoline.
Workup
- additionwas added dropwise a solution
- temperaturecooled condition
- temperaturecooled condition for 2 hours
- stirringfurther stirred at room temperature for 2 hours
- extractionextracted with chloroform
- washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
- dry with materialdried with anhydrous magnesium sulfate
- customChloroform was removed by evaporation
- customthe residue thus obtained
- customwas purified by a silica gel column chromatography (eluent: methylene chloride/methanol=100/1)
Sources & evidence
- ORD record
- ord-02175b25fb674b5eaa3f29157e14cb32
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04738970
Reaction notes
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