Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 206257-39-8 | MDL No. : | MFCD00173367 |
Formula : | C12H9BrClNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YGMLKBFPHVLHGT-UHFFFAOYSA-N |
M.W : | 314.56 | Pubchem ID : | 2764138 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H319 | Packing Group: | |
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 |
---|---|---|
93.8% | With trichlorophosphate; for 1h;Reflux; | Compound 2 (19.4g, 0.O6mol) was suspended in POC13 (45m1) and heated at reflux for 1 hour. The excess solvent was evaporated under reduced pressure and the deep brown residue was taken up in dichloromethane (1 50m1) and washed sequentially by water (1 OOml), saturated sodium bicarbonate (lOOml), and brine (lOOml). The organic phase was dried over sodium sulfate, the solid was filtered off and the filtrate was concentrated to give ethyl 6-bromo-4-chloroquinoline-3-carboxylate (compound 3, 17.67g, 93.8%) as a yellowish solid. |
93.8% | With trichlorophosphate; for 1h;Reflux; | Compound 2 (19.4g, 0.06mol) was suspended in POCI3 (45ml) and heated at reflux for 1 hour. The excess solvent was evaporated under reduced pressure, the deep brown residue was taken up in dichloromethane (150ml) and washed sequentially by water (100ml), saturated sodium bicarbonate (100ml), and brine (100ml). The organic phase was dried over sodium sulfate, the solid was filtered off and the filtrate was concentrated to give ethyl 6-bromo-4-chloroquinoline-3- carboxylate (compound 3, 17.67g, 93.8%) as a yellowish solid. |
88.49% | With trichlorophosphate; at 0 - 110℃; for 3h; | ethyl 6- bromo-4-oxo-1H-quinoline-3-carboxylate (1.5 g, 5.07 mmol, 1.0 eq) was added into POCl3 (15 mL) at 0 C, then stirred for 3 h at 110 C. LCMS showed ~2% starting material was remained. The mixture was cooled to room temperature, concentrated in vacuo to remove excess solvents. The residual was added dropwise into a mixture of ice-water (10 mL) and ethyl acetate (10 mL), separated, extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with 10% NaHCO3, concentrated in vacuo. ethyl 6-bromo-4-chloro-quinoline-3-carboxylate (1.41 g, 4.48 mmol, 88.49% yield) was obtained as a off-white solid. 1H NMR (400MHz, CHLOROFORM-d) d = 9.20 (s, 1H), 8.56 (d, J=2.0 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.91 (dd, J=2.1, 8.9 Hz, 1H), 4.51 (q, J=7.1 Hz, 2H), 1.47 (t, J=7.1 Hz, 3H). |
With thionyl chloride; for 17h;Reflux; | General procedure: The quinolone derivatives 1 were prepared by treating the appropriate aniline (100 mmol) with diethyl ethoxymethylenemalonate (100 mmol) under reflux in ethanol (5 mL) for 2-10 h to obtain the enamine derivatives that were then cyclized in refluxing diphenyl ether for 30 min-6 h [29]. These quinolones (13 mmol) were refluxed in thionyl chloride (20 mL), for 17 h, affording the corresponding chloro-derivatives 2a-g [22]. Reaction of 2a-g (4 mmol) with 2-hydrazinobenzothiazole (8 mmol) in toluene (30 mL), for 3 h, followed by a 2 h reflux in acetic acid gave the corresponding 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones 3a-g as solids which were collected by filtration under vacuum, washed with water and subsequent purified by washing with hot ethyl alcohol. | |
With trichlorophosphate; for 1h;Reflux; Inert atmosphere; Schlenk technique; | General procedure: A solution of compounds 3a-d (1.0 mmol) in POCl3 (6 mL) was refluxed for 1 h. The mixture was evaporated in vacuo and the residue was extracted with methylene chloride, crushed ice and aqueous NH3.The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (SiO2, EA: n-Hex) to get key intermediates 4a-d. |
[ 1379615-56-1 ]
Ethyl 2-bromo-4-chloroquinoline-3-carboxylate
Similarity: 0.87
[ 481054-89-1 ]
Ethyl 6-bromoquinoline-3-carboxylate
Similarity: 0.83
[ 1220418-77-8 ]
Methyl 6-bromoquinoline-3-carboxylate
Similarity: 0.81
[ 1001756-23-5 ]
Methyl 7-bromoquinoline-3-carboxylate
Similarity: 0.81
[ 347146-14-9 ]
Ethyl 8-bromoquinoline-3-carboxylate
Similarity: 0.79
[ 13720-94-0 ]
Ethyl 4-chloroquinoline-3-carboxylate
Similarity: 0.90
[ 1379615-56-1 ]
Ethyl 2-bromo-4-chloroquinoline-3-carboxylate
Similarity: 0.87
[ 77156-85-5 ]
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate
Similarity: 0.86
[ 318685-01-7 ]
Ethyl 4-chloro-6,7-difluoroquinoline-3-carboxylate
Similarity: 0.80
[ 648449-01-8 ]
Methyl 4-chloroquinoline-6-carboxylate
Similarity: 0.79
[ 13720-94-0 ]
Ethyl 4-chloroquinoline-3-carboxylate
Similarity: 0.90
[ 1379615-56-1 ]
Ethyl 2-bromo-4-chloroquinoline-3-carboxylate
Similarity: 0.87
[ 77156-85-5 ]
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate
Similarity: 0.86
[ 481054-89-1 ]
Ethyl 6-bromoquinoline-3-carboxylate
Similarity: 0.83
[ 1001756-23-5 ]
Methyl 7-bromoquinoline-3-carboxylate
Similarity: 0.81
[ 13720-94-0 ]
Ethyl 4-chloroquinoline-3-carboxylate
Similarity: 0.90
[ 1379615-56-1 ]
Ethyl 2-bromo-4-chloroquinoline-3-carboxylate
Similarity: 0.87
[ 77156-85-5 ]
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate
Similarity: 0.86
[ 481054-89-1 ]
Ethyl 6-bromoquinoline-3-carboxylate
Similarity: 0.83
[ 1001756-23-5 ]
Methyl 7-bromoquinoline-3-carboxylate
Similarity: 0.81