Identification | More | [Name]
5-BROMO-QUINOLIN-8-YLAMINE | [CAS]
53472-18-7 | [Synonyms]
53472-18-7 AKOS B015996 AKOS MSC-0726 TIMTEC-BB SBB001595 ART-CHEM-BB B015996 5-BROMO-8-QUINOLINAMINE 5-BROMOQUINOLIN-8-AMINE 5-BROMO-8-AMINOQUINOLINE 8-Amino-5-bromoquinoline (5-bromo-8-quinolyl)amine 8-Quinolinamine, 5-bromo- Quinolin-8-amine, 5-bromo- 5-BROMO-QUINOLIN-8-YLAMINE 5-BROMO-8-QUINOLINAMINE 97% | [Molecular Formula]
C9H7BrN2 | [MDL Number]
MFCD01571832 | [Molecular Weight]
223.07 | [MOL File]
53472-18-7.mol |
Hazard Information | Back Directory | [Synthesis]
4.1.16 Synthesis of 5-bromo-8-aminoquinoline (21): 8-aminoquinoline (1.0 g, 6.94 mmol) was dissolved in 46.0 mL of acetonitrile, and N-bromosuccinimide (NBS, 605 mg, 3.40 mmol for the first portion) was added in batches. The reaction mixture was stirred at 25 °C for 15 min and then the second portion of NBS (667 mg, 3.75 mmol) was added. Stirring of the reaction mixture was continued at 25°C. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in ethyl acetate (EtOAc) and washed with deionized water (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel fast column chromatography (eluent: petroleum ether solution of 10% ethyl acetate) to afford 5-bromoquinolin-8-amine as a yellow amorphous solid in 51% yield.1H NMR (300 MHz, CDCl3) δ 8.76 (d, 1H, J=6.0 Hz), 8.43 (d, 1H, J=9.0 Hz), 7.56 (d, 1H. J=12.0 Hz), 7.48 (q, 1H, J=3.0 Hz), 6.80 (d, 1H, J=6.0 Hz); ESI-MS m/z 222.9 [M+H]+. | [References]
[1] European Journal of Medicinal Chemistry, 2019, p. 290 - 320 [2] Patent: EP3401309, 2018, A1. Location in patent: Paragraph 0859 [3] Patent: WO2010/30722, 2010, A1. Location in patent: Page/Page column 46 [4] Patent: WO2016/77240, 2016, A2. Location in patent: Page/Page column 90; 104 |
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