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CAS No. : | 146564-18-3 | MDL No. : | MFCD11877931 |
Formula : | C10H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 238.08 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; | (c) 8-Bromo-2-(methyloxy)quinoline To a suspension of 8-bromo-2(1H)-quinolinone (2.76 g, 12.32 mmol) in N,N-dimethylformamide (40 ml) under an argon atmosphere at 0C was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | (c) 8-Bromo-2-(methyloxy)quinoline To a suspension of 8-bromo-2(1H)-quinolinone (2.76 g, 12.32 mmol) in N,N-dimethylformamide (40 ml) under an argon atmosphere at 0 C. was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re-extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). | |
74% | To a suspension of 8-bromo-2(lH)-quinolinone (2.76 g, 12.32 mmol) in N5N- dimethylformamide (40 ml) under an argon atmosphere at O0C was added potassium carbonate (3.4 g, 24.63 mmol). The reaction was then stirred for 15 minutes before methyl iodide (0.91 ml, 14.78 mmol) was added. The reaction was allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture was then evaporated and the residue treated with dichloromethane and water. The aqueous fraction was re- extracted with dichloromethane. The combined organic fractions were then dried (MgSO4), the solvent was removed under reduced pressure and then the residue was subjected to chromatography on silica gel using a methanol-dichloromethane gradient. This provided the desired compound as a yellow solid (2.16 g, 74%). MS (ES+) m/z 239 (MH+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In methanol; for 16h;Reflux; | To a solution of <strong>[163485-86-7]8-bromo-2-chloroquinoline</strong> (1) (6.06 g,25 mmol) in 50 mL of methanol, was added sodium methanolate(8.10 g, 150 mmol). The mixturewas refluxed for 16 h, concentratedand partitioned between ethyl acetate and water. The organic layerwas washed with water, dried over MgSO4 and concentrated underreduced pressure to afford compound 4 (97% yield); Mp 87-89 C;1H NMR (300 MHz, CDCl3): delta 7.98 (d, 1H, 8.7 Hz), 7.96 (dd, 1H, 7.8 Hzand 1.2 Hz), 7.69 (dd, 1H, 7.8 Hz and 1.2 Hz), 7.24 (t, 1H, 7.8 Hz), 6.95(d, 1H, 8.7 Hz), 4,16 (s, 3H); MS (APCI, pos. 30 V) m/z: [M+H]+,239.08. |