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| | 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Basic information |
| Product Name: | 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE | | Synonyms: | 6-broMo-1,2,3,4-tetrahydroisoquinolin-1-one;6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE;6-bromo-3,4-dihydroisoquinolin-1(2H)-one;6-BROMO-3,4-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ON;1(2H)-Isoquinolinone, 6-bromo-3,4-dihydro-;6-Bromo-3,4-dihydro-1(2H)-isoquinolinone | | CAS: | 147497-32-3 | | MF: | C9H8BrNO | | MW: | 226.07 | | EINECS: | | | Product Categories: | Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 147497-32-3.mol |  |
| | 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Chemical Properties |
| Melting point | 170.0-173.1 °C | | Boiling point | 453.3±45.0 °C(Predicted) | | density | 1.559±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 14.22±0.20(Predicted) | | form | powder | | color | Yellow |
| | 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Usage And Synthesis |
| Uses | 6-bromo-3,4-dihydroisoquinolin-1(2H)-one is an intermediate used in the synthesis of benzolactams as dopamine D3 receptor ligands.IT is also used in the synthesis of new, selective 3-aminopyrazole based MK2-inhibitors that was proved to inhibit intracellular phosphorylation of hsp27 as well as LPS-induced TNFα release in cells. | | Synthesis | 1. 5-bromo-1-indanone (8a) (1.08 g, 5.1 mmol) was weighed into a 100 mL round bottom flask.
2. dichloromethane (30 mL), methanesulfonic acid (15 mL) and sodium azide (0.5 g, 7.7 mmol) were added sequentially to the reaction flask at 0°C. The reaction was carried out at room temperature.
3. The reaction mixture was stirred at room temperature for 3 hours.
4. Upon completion of the reaction, 1.0 M aqueous sodium hydroxide (50 mL) was slowly added to the reaction solution to quench the reaction.
5. The aqueous phase was extracted with dichloromethane (100 mL x 1) and the organic phases were combined.
6. The organic phase was washed with saturated brine (40 mL×1), dried over anhydrous sodium sulfate and filtered.
7. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, v/v=3:1) to afford 6-bromo-3,4-dihydro-2H-isoquinolin-1-one (8b) as a gray solid (0.45 g, 39% yield). | | References | [1] Patent: US2010/4231, 2010, A1. Location in patent: Page/Page column 67-68
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2670 - 2674
[3] Patent: US2016/251376, 2016, A1. Location in patent: Paragraph 0852; 0853; 0854
[4] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0088
[5] Patent: CN107879975, 2018, A. Location in patent: Paragraph 0132; 0134 |
| | 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Preparation Products And Raw materials |
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