Structure of 1613-37-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1613-37-2 |
Formula : | C9H7NO |
M.W : | 145.16 |
SMILES Code : | [O-][N+]1=C2C=CC=CC2=CC=C1 |
MDL No. : | MFCD00006737 |
InChI Key : | GIIWGCBLYNDKBO-UHFFFAOYSA-N |
Pubchem ID : | 15366 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
With acetic anhydride; at 90℃; for 3h; | Condensation of oxindoles with quinoline-N-oxides: An oxindole (1.6 mmol) may be taken up in acetic anhydride (10 mL) and a solution of quinoline-N-oxide (0.474 mmol) and 5 mL of acetic anhydride may be added. This solution may then be heated at between 0-150°C for between 1-25 hours. In one variation, the reaction is conducted at about 90 °C for about 3 hours. The resulting solution may then be cooled to room temperature. If a solid is observed upon cooling, the material may be isolated by filtration and washed with a minimal amount of cold MeOH, then dried in vacuo. If no solid is observed upon cooling, the reaction may be diluted with an organic solvent, such as ethyl acetate, washed with brine several times, dried over MgSO4 and concentrated to afford an oil. Purification by preparative HPLC may afford a solid product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With p-toluenesulfonyl chloride; In water; at 20℃; for 0.666667h;Sealed tube; Green chemistry; | General procedure: A solution of heterocyclic N-oxide (0.2 mmol), sodium sulfinate (0.2 mmol) and TsCl (49 mg, 0.26 mmol) in H2O (0.5 mL) was stirred under an air atmosphere at ambient temperature for a desired time (monitored by TLC). After the reaction was finished, the mixture was extracted with EtOAc (2 mL x 3) and the organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to obtain product 3. |
80% | With pyridine; tert.-butylhydroperoxide; iron(III) chloride hexahydrate; In water; acetonitrile; at 80℃; for 12h;Schlenk technique; | General procedure: A Schlenk tube (35 ml) equipped with a magnetic bar was loaded with the solution of quinoline N-oxide 1 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and FeCl3*6H2O (20 mol%) in a mixture of CH3CN and H2O (5.0 ml, ca. 9:1 by volume). Then, TBHP (70% in decane, 1.0 mmol) and pyridine (1.0 mmol) were added to the solution dropwise via a syringe and the reaction mixture was stirred at 80 C for 12 h. After the completion of the reaction (monitored by thin layer chromatography), the mixture was washed with brine (15 ml) and then was extracted with dichloromethane (15 ml * 3). The organic phase was combined and then concentrated. The oily crude product was purified by column chromatography using silica gel (-200-300 mesh) as stationary phase and a mixture of petroleum and ethyl acetate as eluent to give the desired product in the noted yields. |
73% | With fluorosulfonyl fluoride; triethylamine; In dimethyl sulfoxide; at 40℃; for 16h; | General procedure: To a 25 mL double-necked flask was added 0.3 mmol of quinoline N-oxide, 0.9 mmol of sodium sulfonate, 1.5 mmol of Et3N, 2.5 mL of DMSO, and bubble SO2F2 into the mixture using a balloon combined with syringe needle. The mixture stirred for 16 h at 40 C. The reaction mixture was diluted with 5 mL of water, and extracted with CH2Cl2 (3*20 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was further purified through flash column chromatography using the mixture of petroleum ether and ethyl acetate as eluent (PE : EA=10 : 1 - 4 : 1). |
68% | With ferric nitrate; In dimethyl sulfoxide; at 120℃; for 0.333333h;Microwave irradiation; | General procedure: Quinoline N-oxides 1 (0.3 mmol), sodium arylsulfinates 2 (0.45 mmol) and Fe(NO3)3 (0.09 mmol) in DMSO (3.0 mL) were added to a microwave reaction tube (5.0 mL). The reaction mixture was heated at 120 C for 20 min under microwave irradiation. After reaction completion, the solvent was distilled under vacuum. Ethyl acetate (10 mL) was added to the residue, and washed with saturated sodium chloride solution (3 × 30 mL). The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:5) as the eluent. All compounds were confirmedby IR, 1H NMR, 13C NMR and MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium permanganate; In acetonitrile; at 90℃; for 1h;Schlenk technique; | General procedure: Quinoline N-oxides 1 (0.3 mmol), arylhydrazines 2 (0.45 mmol), and KMnO4 (0.6 mmol, 94.8 mg) in acetonitrile (3.0 mL) were added to a 25 mL Schlenk tube. The mixture was heated at 90 C for 60 min (monitored by TLC). After completion of the reaction, the solvent was distilled under vacuum. 10 mL ethylacetate was added to the residuum, and 30 mL saturated sodium chloride solution washed three times. The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:3) as eluant. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With potassium permanganate; In acetonitrile; at 90℃; for 1h;Schlenk technique; | General procedure: Quinoline N-oxides 1 (0.3 mmol), arylhydrazines 2 (0.45 mmol), and KMnO4 (0.6 mmol, 94.8 mg) in acetonitrile (3.0 mL) were added to a 25 mL Schlenk tube. The mixture was heated at 90 C for 60 min (monitored by TLC). After completion of the reaction, the solvent was distilled under vacuum. 10 mL ethylacetate was added to the residuum, and 30 mL saturated sodium chloride solution washed three times. The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:3) as eluant. |