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[ CAS No. 178984-56-0 ]

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2D
Chemical Structure| 178984-56-0
Chemical Structure| 178984-56-0
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Product Details of [ 178984-56-0 ]

CAS No. :178984-56-0MDL No. :MFCD06659039
Formula : C16H12ClNO Boiling Point : 414.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :269.73Pubchem ID :22030657
Synonyms :

Computed Properties of [ 178984-56-0 ]

TPSA : 22.1 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.06 Rotatable Bond Count : 3

Safety of [ 178984-56-0 ]

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

Application In Synthesis of [ 178984-56-0 ]

  • Upstream synthesis route of [ 178984-56-0 ]
  • Downstream synthetic route of [ 178984-56-0 ]

[ 178984-56-0 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
79% at 100℃; for 0.166667 h; Microwave irradiation In a 5-mL microwave tube dissolved 7-(benzyloxy)-4-chloroquinoline (0.54 g, 2.002 mmol) in 33percent HBr in AcOH (2 mL). Heated at 100 degrees in microwave for 10 min. Neutralized mixture with saturated NaHC03, extracted into EtOAc, washed organic layer with water then with brine. Dried organic layer with MgSC^, filtered and concentrated to obtain 4- chloroquinolin-7-ol (0.284 g, 1.581 mmol, 79 percent yield) as a white solid
Reference: [1] Patent: WO2014/160203, 2014, A2, . Location in patent: Page/Page column 92
[2] Patent: EP1154774, 2005, B1, . Location in patent: Page/Page column 59
[3] Patent: WO2007/66181, 2007, A2, . Location in patent: Page/Page column 23-24
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YieldReaction ConditionsOperation in experiment
91.6% With trichlorophosphate In toluene at 120℃; for 1 h; Step 3) 7-(benzyloxy)-4-chloroquinoline
To a suspension of 7-(benzyloxy)quinolin-4-ol (72 g, 287 mmol) in toluene (134 mL) was added phosphoryl trichloride (44 g, 287 mmol, Tianjin FuChen Chem. Co. Ltd.).
The suspension was heated to 120° C. for 1 hour.
The reaction mixture was then cooled to 70° C. and diluted with EtOAc (600 mL).
The resulted mixture was stirred for 30 minutes while cooling down to 15° C. using an ice bath.
The mixture was neutralized with 3 M NaOH aqueous solution to pH 7~8 while maintaining the temperature of the solution under 20° C.
The aqueous layer was separated and extracted with EtOAc (200 mL).
The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a pale yellow solid (70.8 g, 91.6percent).
MS (ESI, pos. ion) m/z: 270.1 [M+1];
1H NMR (400 MHz, DMSO-d6): δ 5.31 (s, 2H), 7.35 (t, 1H), 7.42 (t, J=7.2 Hz, J=7.6 Hz, 2H), 7.47 (dd, J=2.8 Hz, J=9.2 Hz, 1H), 7.52 (d, J=7.6 Hz, 2H), 7.13 (t, J=4.8 Hz, J=4.0 Hz, 2H), 8.11 (d, J=9.6 Hz, 1H), 8.75 (d, J=4.8 Hz, 1H).
Reference: [1] Patent: US2012/219522, 2012, A1, . Location in patent: Page/Page column 20
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  • [ 100-39-0 ]
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YieldReaction ConditionsOperation in experiment
46.8% With potassium carbonate In acetone at 20℃; To a 100 ml round bottom flask was added 4-chloro-7-hydroxyquinoline (0.89 g, 5 mmol), acetone (40 ml), benzyl bromide(7.5 mmol) and anhydrous K2C03 (2. Og)The reaction was stirred at room temperature,TLC trace detection.After completion of the reaction, acetone was distilled off under reduced pressure, 150 mL of water was added,Extracted with ethyl acetate, the organic phase was combined, acidified with concentrated hydrochloric acid and anhydrous ethanol was added to give a dark oilThe crystals were recrystallized from acetone and the crystals were precipitated and filtered and basified to give a white solid (0.63 g, yield 46.8percent)
46.8% With potassium carbonate In acetone at 20℃; A 100 ml round bottomed flask was charged with 4-chloro-7-hydroxyquinoline (0.89 g, 5 mmol), acetone (40 ml), benzyl bromide(7.5 mmol) and anhydrous K2CO3 (2.0 g). The reaction was stirred at room temperature and checked by TLC.After completion of the reaction, the acetone was distilled off under reduced pressure, 150 mL of water was added and the mixture was extracted with ethyl acetate. The combined organic phases were acidified with concentrated hydrochloric acid and brought to absolute ethanol with water to give a dark oil. The crystals were recrystallized from acetone to precipitate crystals. To give a white solid (0.63 g, 46.8percent yield).
0.5 g With sodium hydride In N,N-dimethyl-formamide at 20℃; General procedure: A mixture of 4-chloroquinolin-7-ol 8 (0.72g, 4mmol) and anhydrous DMF (10mL) was stirred at room temperature until clear, and then, 60percent NaH (0.4g, 10mmol) and halogenated alkane (20–30mmol) were added. The mixture was stirred at room temperature. After completion of the reaction as indicated by TLC, the solution was poured into H2O (100mL) and extracted with ethyl acetate. The organic phase was made acidic with concentrated hydrochloric acid. Upon removal of solvent, the residue was crystallized from acetone to afford a yellow solid. The solid was dissolved in water and made basic with sodium bicarbonate, and the aqueous mixture was extracted with ethyl acetate. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil was purified by column chromatography using a mixture of dichloromethane and methanol 100:1 as the eluent to successfully afford the target products 9a-k in good yield.
Reference: [1] Patent: CN105037266, 2017, B, . Location in patent: Paragraph 0323-0324; 0339-0340
[2] Patent: CN105017145, 2017, B, . Location in patent: Paragraph 0327; 0342; 0343
[3] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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Reference: [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 83
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Reference: [1] Patent: WO2005/63739, 2005, A1, . Location in patent: Page/Page column 101
[2] Patent: US2012/219522, 2012, A1,
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Reference: [1] Patent: CN105037266, 2017, B,
[2] Patent: CN105017145, 2017, B,
[3] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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Reference: [1] Patent: US2012/219522, 2012, A1,
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Reference: [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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Reference: [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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  • [ 56881-19-7 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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  • [ 71083-05-1 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2019, p. 666 - 678
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  • [ 1394820-98-4 ]
Reference: [1] Patent: US2012/219522, 2012, A1,
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6277 - 6292
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