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[ CAS No. 4295-04-9 ]

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2D
Chemical Structure| 4295-04-9
Chemical Structure| 4295-04-9
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Product Details of [ 4295-04-9 ]

CAS No. :4295-04-9MDL No. :MFCD00024007
Formula : C10H8ClNO Boiling Point : 299.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :193.63Pubchem ID :228348
Synonyms :

Computed Properties of [ 4295-04-9 ]

TPSA : 22.1 H-Bond Acceptor Count : 2
XLogP3 : 2.8 H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 1

Safety of [ 4295-04-9 ]

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 [ 4295-04-9 ]

  • Upstream synthesis route of [ 4295-04-9 ]
  • Downstream synthetic route of [ 4295-04-9 ]

[ 4295-04-9 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
67% With water; hydrogen iodide In dichloromethane at 100℃; for 5 h; Synthesis of 2-((4-chloroquinolin-6-yl)oxy)acetonitrile: To a stirred solution of 4-chloro-6-methoxyquinoline (500 mg, 2.5 mmol) in DCM (10mL) was added aqueous HI (5 mL, 45 percent). The mixture was heated to 100 °C and stirred for 5 hours. The solution was allowed to cool to room temperature and water (20 mL) was added. The organic phase was separated,and aqueous phase was basified and extracted with DCM (30 mL×3). The organic phase was combined and washed with water and brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give 4-chloroquinolin-6-ol (300mg, 67percent) as white solid used in next step directly. LC-MS (ESI) m/z = 180.3 (M+H). Bromoacetonitrile (240 mg, 2.0 mmol) and Cs2CO3 (350 mg, 2.5 mmol) was added to a solution of the obtained 4-chloroquinolin-6-ol (300 mg,1.7 mmol) in DMF (10 mL). The reaction mixture was heated to 60 °C and stirred for 3 hours. The solution was allowed to cool to room temperature and water (50mL) was added. The mixture was extracted with EtOAc (50 mL×3), and the organic phase was combined and washed with water and brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give 2-((4-chloroquinolin-6-yl)oxy)acetonitrile (300 mg, 81percent) as an off white solid. LC-MS(ESI) m/z = 219.1 (M+H). Following general procedure A using 2-((4-chloroquinolin-6-yl)oxy)acetonitrilein step 1, 30 was obtained as an off white solid. 1H NMR (400 MHz, CD3OD)δ 8.49 (d, J = 4.9 Hz, 1H), 7.95 (d, J = 9.2 Hz, 1H), 7.65 (d, J = 2.8 Hz, 1H), 7.51 (dd, J = 9.2, 3.0 Hz, 1H), 7.44 (d, J = 4.4 Hz, 1H), 5.20 (s, 2H), 2.97-3.02(m, 2H), 2.27-2.41 (m, 3H), 2.05-2.08 (m, 1H). LC-MS (ESI) m/z = 313.1 (M-H).
56% With sodium hydroxide; hydrogen bromide In water A.
4-Chloroquinolin-6-ol
A solution of 4.99 g (18.1 mmol) of 4-chloro-6-methoxyquinoline and 50 mL of 48percent hydrobromic acid is heated under reflux for seven hours.
Upon cooling to room temperature, the reaction solution afforded a dark solid that was then slurried in water.
The aqueous mixture was adjusted to pH 10 by the addition of 4N sodium hydroxide.
The resulting solid was filtered, washed with water and air-dried to give 1.83 g (56percent) of 4-chloroquinolin-6-ol: m.p. 223° C.
300 mg With hydrogen iodide In dichloromethane at 100℃; for 5 h; 4-chloro-6-methoxyquinoline 4a (500 mg, 2.5 mmol) was dissolved in 10 mL of dichloromethane, and hydroiodic acid (45percent, 5 mL) was added dropwise. Upon completion of the addition, the reaction solution was heated to 100° C. and stirred for 5 hours. 20 mL of water was added to the reaction solution, and the organic phase was separated. The aqueous phase was added dropwise with saturated sodium carbonate solution to adjusted the pH to 89, and extracted with dichloromethane (30 mL×3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 4-chloroquinolin-6-ol 24a (300 mg, a white solid), which was used directly in the next step.
300 mg With hydrogen iodide In dichloromethane at 100℃; for 5 h; 4-chloro-6-methoxyquinoline 4a (500 mg, 2.5 mmol) was dissolved in 10 mL of dichloromethane, and hydroiodic acid (45percent, 5 mL) was added dropwise. Upon completion of the addition, the reaction solution was heated to 100° C. and stirred for 5 hours. 20 mL of water was added to the reaction solution, and the organic phase was separated. The aqueous phase was added dropwise with saturated sodium carbonate solution to adjusted the pH to 89, and extracted with dichloromethane (30 mL×3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 4-chloroquinolin-6-ol 24a (300 mg, a white solid), which was used directly in the next step. (0288) MS m/z (ESI): 328.3 [M+1]

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 277 - 282
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 1659,1660
[3] Justus Liebigs Annalen der Chemie, 1950, vol. 568, p. 73,79
[4] Patent: US5506235, 1996, A,
[5] Patent: KR2016/6207, 2016, A, . Location in patent: Paragraph 0516; 0519-0522
[6] Patent: US2016/108035, 2016, A1, . Location in patent: Paragraph 0286-0287
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  • [ 6563-13-9 ]
  • [ 13676-02-3 ]
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Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795
[2] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132
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  • [ 23432-39-5 ]
Reference: [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 1896,1904[2] Chem. Zentralbl., 1938, vol. 109, # I, p. 3774
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