* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the Chemical Society, 1948, p. 893
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 277,280
2
[ 25253-09-2 ]
[ 23432-44-2 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 4, p. 1015 - 1018
3
[ 36053-94-8 ]
[ 23432-44-2 ]
Reference：
[1] Patent: US2558211, 1949, ,
4
[ 77156-75-3 ]
[ 23432-44-2 ]
Reference：
[1] Journal of the Chemical Society, 1948, p. 893
5
[ 19146-73-7 ]
[ 23432-44-2 ]
Reference：
[1] Journal of the Chemical Society, 1948, p. 893
6
[ 23432-44-2 ]
[ 36075-68-0 ]
Yield
Reaction Conditions
Operation in experiment
95%
With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere
Into a 100-mL round-bottom flask, was placed 8-methylquinolin-4-ol (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 hours at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with NaOH (2 mol/L). The precipitated solids were collected by filtration. This resulted in 660 mg (95percent) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+l] : 222&224.
4-hydroxy-8-methyl-3-methylthiomethylquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With formaldehyd; In ethanol; triethylamine;
(a) To a stirred suspension of 4-hydroxy-8-methylquinoline (10.0 g.) in triethylamine (8.8 ml.) and industrial methylated spirit (15 ml.) at 0-5 was added methanethiol (10.4 ml.) followed by aqueous formaldehyde (40%, 14.2 ml.). The mixture was stirred and boiled under reflux for 30 hours. Aqueous formaldehyde (40%, 14.2 ml.) was added dropwise to a stirred solution of triethylamine (8.8 ml.) and methanethiol (10.4 ml.) in ethanol (15 ml.), maintaining the temperature below 10. The resulting solution was added to the above reaction mixture and the mixture was stirred and boiled under reflux for 20 hours. The mixture was left to cool overnight. The resulting crystalline solid was collected by filtration to give the novel compound 4-hydroxy-8-methyl-3-methylthiomethylquinoline, m.p. 226-228.
With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
Into a 100-mL round-bottom flask, was placed <strong>[23432-44-2]8-methylquinolin-4-ol</strong> (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 hours at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with NaOH (2 mol/L). The precipitated solids were collected by filtration. This resulted in 660 mg (95%) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+l] : 222&224.
95%
With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃; for 15.0h;
Into a lOO-mL round-bottom flask, was placed <strong>[23432-44-2]8-methylquinolin-4-ol</strong> (500 mg, 3.14 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of tribromophosphane (851 mg, 3.14 mmol, 1.20 equiv) dropwise with stirring at room temperature. The resulting solution was stirred for 15 h at room temperature. The reaction was then quenched by the addition of water/ice (100 mL). The pH value of the solution was adjusted to 10 with sodium hydroxide (2 mol/L). The solids were collected by filtration. This resulted in 660 mg (95%) of 4-bromo-8-methylquinoline as a light yellow solid. MS (ES, m/z) [M+H]+: 222.
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