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CAS No. : | 3033-80-5 | MDL No. : | MFCD00034436 |
Formula : | C11H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OQXVXPBDSJQYRR-UHFFFAOYSA-N |
M.W : | 173.21 | Pubchem ID : | 316986 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
93% | With selenium(IV) oxide; In 1,4-dioxane; for 3h;Reflux; | The 2-methyl-8-methoxy quinoline (10) (3.50g, 20 . 2mmol) by adding 50 ml of dioxane, stirring to dissolve, then adding selenium dioxide (2.20g, 19 . 9mmol), heating reflow 3h. Cooling, filtering, adding activated carbon to the filtrate (1.0g), micro boils 15 min. Is filtered, concentrated under reduced pressure, to obtain yellow solid 3.52g, yield 93%. |
93% | With selenium(IV) oxide; In 1,4-dioxane; for 4h;Reflux; | 2-Methyl-8-methoxyquinoline (2) (3.50 g, 20.2 mmol) was addedDissolved in 80 mL of dioxane, followed by addition of selenium dioxide (2.20 g, 19.9 mmol) and heating under reflux for 4 h. Cooling, filtering, to the filtrate by adding activated carbon (4.0g), micro-boiling 10min. Filtered hot and concentrated under reduced pressure to give 3.52 g of a yellow solid in 93% yield, m.p. 103-104 C (103C). |
81% | With selenium(IV) oxide; In 1,4-dioxane; at 110℃; for 2h; | 8-Methoxy-2-methylquinoline (24) (28.9 mmol) was reacted withSeO2 (52.0 mmol, 1.8 eq) in anhydrous 1,4-dioxane (500 mL) at 110 Cfor 2 h to give 8-methoxyquinoline-2-carboxaldehyde (25). After completionof the reaction; the inorganic compounds were filtered off andpoured into cold water and partitioned with chloroform. The chloroformlayer was concentrated and the crude product obtained was purifiedby column chromatography over silica gel (60-120) usingchloroform as eluent. 8-Methoxyquinoline-2-carbaldehyde (25): yellow solid, yield 81%,m.p. 102-104 C; 1H NMR (CDCl3, 400 MHz): δ 10.32 (s, 1H), 8.29 (d,1H, J=8.4 Hz), 8.08 (d, 1H, J=8.4 Hz), 7.63 (t, 1H, J=8.0 Hz), 7.48(d, 1H, J=8.2 Hz), 7.16 (d, 1H, J=7.8 Hz), 4.17 (s, 3H); 13C NMR(CDCl3, 100 MHz): δ 193.7, 156.1, 151.5, 139.9, 137.3, 131.4, 129.8,119.6, 118.0, 108.6, 56.4; ESI-MS found m/z 187.98 [M+H]+. |
With selenium(IV) oxide; In 1,4-dioxane; at 60 - 120℃; for 2.5h; | General procedure: o-Anisidine (29) (81.2 mmol) dissolved in 6 M HCl (190The resultant mixture was stirred for 5 min at a temperatureof 100C. Further, crotonaldehyde (30) (162.4 mmol, 2.0equiv.) was added to the reaction mixture dropwise followedby heating at 120C for 3 h. The aqueous layer was extractedwith chloroform after cooling and neutralization by aqueousNaOH solution. The organic layer was dried and purified bycolumn chromatography (silica gel 60-120 , chloroform aseluent) to get 8-methoxy-2-methylquinoline (31)26,27. It wasoxidized using SeO2 in 1,4-dioxane using the above-mentionedprocedure to obtain 8-methoxyquinoline-2-carbaldehyde(32). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-Bromo-8-methoxy-2-methylquinoline 8-Methoxy-2-methylquinoline (7.92 g) was dissolved in methanol (80 mL), and bromine (2.37 mL) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 1.5 hours. To the reaction liquid was added a saturated aqueous sodium thiosulfate solution and further added a saturated aqueous sodium hydrogen carbonate solution, followed by evaporating methanol under reduced pressure. This aqueous solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in this order, and then dried over anhydrous sodium sulfate. After evaporating the solvent, the desired product (47.6 g) was obtained as a yellow powder. 1H NMR (CDCl3, 400 MHz): delta 2.83 (3H, s), 4.07 (3H, s), 6.92 (1H, d, J=8.6 Hz), 7.42 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=8.6 Hz), 8.38 (1H, d, J=8.6 Hz). | ||
5-Bromo-8-methoxy-2-methylquinoline Commercially available 8-methoxy-2-methylquinoline (7.92 g) was dissolved in methanol (80 mL), and bromine (2.37 mL) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 1.5 hours. To the reaction liquid was added a saturated aqueous sodium thiosulfate solution and further added a saturated aqueous sodium hydrogen carbonate solution, followed by evaporating methanol under reduced pressure. This aqueous solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the desired product (47.6 g) as a yellow powder. 1H-NMR (CDCl3, 400 MHz): delta 2.83 (3H, s), 4.07 (3H, s), 6.92 (1H, d, J=8.6 Hz), 7.42 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=8.6 Hz), 8.38 (1H, d, J=8.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With toluene-4-sulfonamide; In toluene; at 120℃; for 12h;Inert atmosphere; | A solution of 8-methoxy-2-methylquinoline (100 mg, 0.57 mmol), p-toluenesulfonamide (98.85 mg, 0.57 mmol) and pyrazine-2-carbaldehyde (61.5 mg, 0.57 mmol) in toluene (0.5 mL) was refluxed at 120° C. for 12 h in a reaction tube under nitrogen. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure. Then the concentrate was purified by column chromatography with EtOAc/DCM (1:2, v/v) on silica gel, affording TZ-23-14 (130 mg, 87percent). 1H-NMR (400 MHz, CDCl3): delta 8.89-8.71 (m, 1H), 8.57 (dt, J=2.7, 1.4 Hz, 1H), 8.44 (t, J=2.1 Hz, 1H), 8.07 (dd, J=17.8, 12.4 Hz, 2H), 7.83-7.66 (m, 2H), 7.53-7.32 (m, 2H), 7.06 (d, J=7.6 Hz, 1H), 4.09 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 155.28, 153.59, 150.80, 144.47, 144.17, 143.33, 140.45, 136.65, 135.01, 129.66, 128.82, 127.03, 120.64, 119.43, 108.06, 56.15. |
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