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CAS No. : | 4360-63-8 | MDL No. : | MFCD00003214 |
Formula : | C4H7BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CKIIJIDEWWXQEA-UHFFFAOYSA-N |
M.W : | 167.00 | Pubchem ID : | 78068 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235 | UN#: | N/A |
Hazard Statements: | H315-H319-H227 | 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 |
---|---|---|
To 20 mL of an N,N-dimethylformamide solution containing 540 mg of <strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>, 376 mg of 60% sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Thereto was added 3.2 mL of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90C for 16 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate : hexane = 1 : 1] to obtain 165 mg of a white solid, 1-(1,3-dioxolan-2-ylmethyl)-<strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>. 1H-NMR (CDCl3) delta: 3.84-3.92 (2H, m), 3.99-4.05 (2H, m), 4.54 (2H, d, J=4.4 Hz), 5.25 (1H, t, J=4.4 Hz), 6.91 (1H, s), 7.24-7.37 (1H, m), 7.60-7.68 (2H, m), 8.02 (1H, d, J=7.9 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 30 mL of an N,N-dimethylformamide solution containing 1.5 g of <strong>[101382-55-2]7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde</strong>, 0.32 g of 60% sodium hydride was added, and the mixture was stirred at 50C for 30 minutes. Thereto was added 1.53 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred at 80 to 90C for 2 hours. Thereto was added 1.53 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred for 3 hours and 30 minutes. Water and ethyl acetate were then added thereto, and the reaction mixture was adjusted to pH 1.5 with 6 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was added with a mixed solution of diethyl ether and ethyl acetate, and a solid substance collected by filtration, and then purified by silica gel column chromatography [eluent; chloroform] to obtain 0.35 g of a yellow solid, 1-(1,3-dioxolan-2-ylmethyl)-<strong>[101382-55-2]7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde</strong>. 1H-NMR (CDCl3) delta: 3.88-3.93 (2H, m), 3.95 (3H, s), 4.00-4.10 (2H, m), 4.56 (2H, d, J=4.3 Hz), 5.26 (1H, t, J=4.3 Hz), 6.88 (1H, dd, J=8.8, 2.2 Hz), 7.09 (1H, d, J=2.2 Hz), 7.63 (1H, d, J=8.8 Hz), 8.32 (1H, s), 10.42 (1H, s) |
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