6-BROMO-3-CHLOROISOQUINOLINE synthesis
- Product Name:6-BROMO-3-CHLOROISOQUINOLINE
- CAS Number:552331-06-3
- Molecular formula:C9H5BrClN
- Molecular Weight:242.5
552331-05-2
552331-06-3
General procedure for the synthesis of 6-bromo-3-chloroisoquinoline from 6-bromo-1,3-dichloroisoquinoline: a mixture of 6-bromo-1,3-dichloroisoquinoline (1.8 g, 6.5 mmol), red phosphorus (0.48 g, 15.5 mmol), and hydriodic acid (3 ml, 48%) in acetic acid (20 ml) was heated and refluxed for 8 hours. After completion of the reaction, it was filtered while hot and the filtrate was concentrated under reduced pressure. The concentrated residue was alkalized by addition of sodium hydroxide solution and subsequently extracted with ethyl acetate (200 mL). The organic phase was washed with saturated saline, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel fast column chromatography to afford 6-bromo-3-chloroisoquinoline (0.81 g, 50% yield) using 30% ethyl acetate/hexane as eluent. Mass spectrum (DCI/NH3) m/e 244 (M+H)+.
552331-05-2
84 suppliers
$45.00/100mg
552331-06-3
92 suppliers
$43.00/100mg
Yield:552331-06-3 68.4%
Reaction Conditions:
with phosphorus;acetic acid at 120; for 5 h;Temperature;
Steps:
4
Add 50 g of 1,3-dichloro-6-bromoisoquinoline to 500 mL of glacial acetic acid, and then add 14 g of red phosphorus.Hydrochloric acid 100 mL, then the system was heated to reflux, the reaction was about 5 h, and TLC confirmed the reaction was complete.After-treatment: cool to room temperature, suction filtration, add 500 mL of water to the filter cake.The mixture was adjusted to pH = 8 with 15% aqueous ammonia, filtered, and the filtrate was extracted with ethyl acetate.The acetic acid phase is dried, added with water and alkali, extracted with ethyl acetate, and combined with all organic phases.Wash once with saturated brine, dry over anhydrous sodium sulfate, spin dry,The column was passed through 200-300 mesh silica gel, petroleum ether: ethyl acetate = 50:1 to 20:1.The product 3-chloro-6-bromoisoquinoline 30 g was obtained in a yield of 68.4%.
References:
Shanghai Handao Pharmaceutical Technology Co., Ltd.;Jiang Yongjun CN108929270, 2018, A Location in patent:Paragraph 0017; 0019; 0022; 0024; 0027; 0029; 0032; 0034
943749-63-1
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552331-06-3
92 suppliers
$43.00/100mg
501130-49-0
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$229.00/100mg
552331-06-3
92 suppliers
$43.00/100mg