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Chemical Structure| 723280-94-2 Chemical Structure| 723280-94-2

Structure of 723280-94-2

Chemical Structure| 723280-94-2

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Product Details of [ 723280-94-2 ]

CAS No. :723280-94-2
Formula : C9H5BrN2O3
M.W : 269.05
SMILES Code : OC1=C([N+]([O-])=O)C=NC2=CC(Br)=CC=C12
MDL No. :MFCD17170311
InChI Key :QJMLADCOCGDUQT-UHFFFAOYSA-N
Pubchem ID :21984407

Safety of [ 723280-94-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 723280-94-2 ]

* 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.

  • Downstream synthetic route of [ 723280-94-2 ]

[ 723280-94-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 723280-94-2 ]
  • [ 723280-98-6 ]
YieldReaction ConditionsOperation in experiment
81% With trichlorophosphate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere; 7-Bromo-3-nitroquinolin-4-ol (400, 3.8 g, 14.12 mmol) was suspended in POCb (20 mL). Anhydrous DMF (1 mL) was added. The mixture was then heated to 120C under an atmosphere of nitrogen for 3 hours at which time the reaction was cooled to room temperature. The precipitate was collected by filtration, washed with water, and then partitioned between CH2CI2 (60 mL) and a saturated aqueous solution of Na2C03. The organic layer was separated, washed with brine, dried over Na2S04, filtered, and concentrated to afford 3.3 g (1 1.5 mmol, 81%) of 7-bromo-4-chloro-3-nitroquinoline (401) as a beige-colored solid. (ES, m/z): [M+H]+ = 287.1 / 288.9.
81% With trichlorophosphate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere; 7-Bromo-3-nitroquinolin-4-ol (3.8 g, 14.12 mmol) was suspended in POCh (20 mL). Anhydrous DMF (1 mL) was added. The mixture was then heated to 120C under an atmosphere of nitrogen for 3 hours at which time the reaction was cooled to room temperature. The precipitate was collected by filtration, washed with water, and then partitioned between CH2CI2 (60 mL) and a saturated aqueous solution of Na2C03. The organic layer was separated, washed with brine, dried over Na2S04, filtered, and concentrated to afford 3.3 g (11.5 mmol, 81%) of 7-bromo-4-chloro-3- nitroquinoline as a beige-colored solid. (ES, m/z): [M+H]+ = 287.1 / 288.9.
With trichlorophosphate; at 102℃; for 0.75h; 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol)) was suspended in POC13 (130 ML) and brought to 102C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H2O, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (LX), dried over NA2S04, filtered, and concentrated to afford 33.7 g of 7-bromo-4-chloro-3-nitroquinoline as a beige solid. 1H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8.41 (d, J= 1.8 Hz, 1H), 8.30 (d, J= 9. 0 HZ, 1H), 7.90 (dd, J = 8. 9,2. 1 HZ, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol) ) was suspended in POC13 (130 mL) and brought to 102C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H20, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (1x), dried over Na2S04, filtered, and concentrated to afford 33.7 g of 7-bromo-4-chloro-3- nitroquinoline as a beige solid.
D7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed withH20, and then partitioned withCHzClz (3 L) and 2MNa2CO3 (500 mL). The organic layer was separated, washed withH20(lx), dried overNa2S04, filtered, and concentrated under reduced pressure to afford 33.7 g of 7-bromo-4-chloro-3-nitroquinoline as a beige solid. 'H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8.41 (d, J= 1. 8 Hz, 1H), 8. 30 (d, J= 9.0 Hz, 1H), 7.90 (dd, J= 8.9, 2.1 Hz, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed with H20, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H2O (lx), dried over Na2S04, filtered, and concentrated under reduced pressure to afford 33.7 g of 7-bromo-4- chloro-3-nitroquinoline as a beige solid. 'H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8. 41 (d, J= 1. 8 Hz, 1H), 8. 30 (d, J= 9.0 Hz, 1H), 7.90 (dd, J= 8.9, 2.1 Hz, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed with H2O, and then partitioned with CHZCLZ (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (LX), dried over NA2S04, filtered, and concentrated to afford 33.7 g of 7- BROMO-4-CHLORO-3-NITROQUINOLINE as a beige solid.
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 15 - 100℃; for 16h; General procedure: To a mixture of 6-bromo-3-nitro-quinoline-2,4-diol (30 g, 105.24 mmol, 1 eq) in POCh (484.12 g, 3.16 mol, 293.41 mL, 30 eq) was added N,N-diisopropylethylamine (40.81 g, 315.73 mmol, 55.00 mL, 3 eq) slowly at l 5C. The mixture was stirred at 100 C for 16 hrs. The mixture was concentrated in vacuum. The residue was poured into ice water (2000 mL), filtered and washed with H2O (500 mL x 3), and dried to provide 6-bromo-2,4-dichloro-3- nitro-quinoline (30 g, 93.18 mmol, 88.54% yield) as a yellow solid.

 

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