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CAS No. : | 1078-28-0 | MDL No. : | MFCD00006761 |
Formula : | C11H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NAGJQQFMJKMXJQ-UHFFFAOYSA-N |
M.W : | 173.21 | Pubchem ID : | 70648 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
83% | With acetic anhydride; at 150℃; for 30h; | General procedure: A mixture of 2-methylquinoline (5a, 0.14 g, 1 mmol), <strong>[92-55-7](5-nitrofuran-2-yl)methylene diacetate</strong> (0.72 g, 3 mmol) and acetic anhydride (30 mL) was heated at 150 C for 30 h (TLC monitoring). After cooling, the solvent was removed in vacuo to provide the crude product, which was purified by flash column chromatography (FC, silica gel use CH2Cl2 as eluent) to give 6a (0.22 g, 81%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With toluene-4-sulfonamide; In toluene; at 120℃; for 12h;Inert atmosphere; | A solution of 6-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-23-12 (127 mg, 85percent). 1H-NMR (400 MHz, CDCl3): delta 8.73 (d, J=1.3 Hz, 1H), 8.61-8.48 (m, 1H), 8.41 (d, J=2.5 Hz, 1H), 7.99 (dd, J=15.6, 8.9 Hz, 2H), 7.81 (dd, J=70.7, 15.9 Hz, 2H), 7.56 (d, J=8.5 Hz, 1H), 7.44-7.29 (m, 1H), 7.02 (d, J=2.8 Hz, 1H), 3.90 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 158.00, 152.10, 150.82, 144.45, 144.36, 144.25, 143.24, 135.23, 134.77, 130.93, 128.79, 128.40, 122.74, 120.91, 104.99, 55.53. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyrrolidine; potassium-t-butoxide; In tetrahydrofuran; at 80℃; under 760.051 Torr; for 16h; | General procedure: A coupling reaction between <strong>[6563-13-9]6-methoxyquinoline N-oxide</strong> (1a) and trimethylsulfonium iodide (2a) was performed. The results are shown in Table 1.As a result of screening various bases and solvents, the use of KOtBu base in THF promotes the coupling of 1a and 2a to be redox-neutral ( redox-neutral) and the reductive C2-methylated products 3a and 3aa were found to give in good yields (71%).After further optimization, it was found that the use of pyrrolidine as an additional base promotes a high level of yield (91%) and selectivity (15:1 ratio) for the production of 3a (entry 6).From the control entry 9, it was confirmed that the combination of KOtBu and pyrrolidine was essential for the binding of 1a and 2a.In addition, as shown in entry 10, 3a was formed in 95% yield within 3 hours with high chemical selectivity (18: 1).Satisfyingly, this transformation proceeded under mild reaction conditions (40 C.) to afford 3a with a selectivity of 20:1 ratio in 92% yield (entry 11).In addition, as a result of carrying out this reaction on a scale of 1 g, 3a was obtained in 84% yield with almost the same chemical selectivity of 20:1 (entry 12). |
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