[ CAS No. 53472-18-7 ]

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2D
Chemical Structure| 53472-18-7
Chemical Structure| 53472-18-7
Structure of 53472-18-7

Quality Control of [ 53472-18-7 ]

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Related Doc. of [ 53472-18-7 ]

SDS

Product Details of [ 53472-18-7 ]

CAS No. :53472-18-7MDL No. :MFCD01571832
Formula :C9H7BrN2Boiling Point :353.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :223.07Pubchem ID :613829
Synonyms :

Computed Properties of [ 53472-18-7 ]

TPSA : 38.9 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 53472-18-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53472-18-7 ]

  • Upstream synthesis route of [ 53472-18-7 ]
  • Downstream synthetic route of [ 53472-18-7 ]

[ 53472-18-7 ] Synthesis Path-Upstream   1~3

  • 1
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  • [ 53472-18-7 ]
YieldReaction ConditionsOperation in experiment
51% With N-Bromosuccinimide In acetonitrile at 25℃; for 1.25 h; 4.1.16
5-Bromo-8-aminoquinoline (21)
To solution of compound 12 (1.0 g, 6.94 mmol) in 46.0 mL of acetonitrile, a portion of NBS (605 mg, 3.40 mmol) was added.
The reaction mixture was stirred at 25 °C for 15 min, then a second portion of NBS (667 mg, 3.75 mmol) was added.
The reaction was stirred for 1 h at 25 °C.
The solvent was evaporated under reduced pressure and the residue taken up with EtOAc and washed with water (3 * 50 mL).
The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated.
The residue was purified by flash chromatography on silica gel (10percent EtOAc in petroleum ether) to afford the title compound as an amorphous yellow solid (51percent 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), 7.48 (q, 1H, J = 3.0 Hz), 6.80 (d, 1H, J = 6.0 Hz); ESI-MS m/z 222.9 [M+H]+.
50% With N-Bromosuccinimide In acetone at 20℃; for 0.50 h; Quinolin-8-amine (0.20 g, 1.38 μMol) was dissolved in acetonitrile (20 mL), and N-bromosuccinimide (0.26 g,1.43 μMol) was added to the solution. The mixture was stirred at room temperature for 30 minutes. Water was addedto the mixture. The organic layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentratedunder reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 90/10-> 70/30) to obtain compound 117-1 (0.15 g, 50percent).1H NMR (300 MHz, DMSO-d6, δ): 8.76 (d, J = 3.3 Hz, 1H), 8.42 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.48 (dd,J = 8.4, 4.2 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 5.04 (br, 2H).
760 mg With N-Bromosuccinimide In acetonitrile at 20℃; for 2.00 h; To a solution of 8-aminoquinoline (1 g, 4.8 mmol) in CH3CN (30 mL) were added NBS (1.28 g, 7.2 mmol). The reaction mixture was stirred at RT for 2 hour. The residue was treated with water and extracted with EA. The extracts were concentrated and the residue purifiled by silica gel chromatography to afford 5-bromo-8-quinolylamine (760 mg).
Reference: [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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  • [ 578-66-5 ]
  • [ 53472-18-7 ]
  • [ 36107-02-5 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 7, p. 1782 - 1788
[2] Letters in Drug Design and Discovery, 2017, vol. 14, # 12, p. 1415 - 1424
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 386[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 269
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