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[ CAS No. 52311-50-9 ]

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2D
Chemical Structure| 52311-50-9
Chemical Structure| 52311-50-9
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Product Details of [ 52311-50-9 ]

CAS No. :52311-50-9MDL No. :MFCD00234316
Formula : C7H8ClNO Boiling Point : 230.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :157.60Pubchem ID :817238
Synonyms :

Computed Properties of [ 52311-50-9 ]

TPSA : 22.1 H-Bond Acceptor Count : 2
XLogP3 : 2.2 H-Bond Donor Count : 0
SP3 : 0.29 Rotatable Bond Count : 2

Safety of [ 52311-50-9 ]

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

Application In Synthesis of [ 52311-50-9 ]

  • Upstream synthesis route of [ 52311-50-9 ]
  • Downstream synthetic route of [ 52311-50-9 ]

[ 52311-50-9 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
92% at 0 - 25℃; for 12 h; A mixture of 2-chloro-4-nitropyridine (170 g 1070 mmol) in THF (2 L) was added NaOEt (109.45 g 1610 mmol) slowly at 0 . The mixture was stirred at 25 for 12 h. LCMS and TLC (PE/EA 51 Rf 0.6) showed the reaction was finished. The mixture was filtered and most solvent of the filtrate was removed in vacuo. The residue was extracted with EA (800 mL x 3) and the organic layer was washed with saturated NaCl solution (1 L) dried over Na2SO4and concentrated to give 2-chloro-4-ethoxypyridine (157 g 1.0 mol 92yield) as a solid1HNMR(400 MHz CD3OD) δ 8.15 (d J 6.0 Hz 1H) 6.99 (d J 2.0 Hz 1H) 6.91-6.89 (m 1H) 4.16-4.14 (m 2H) 1.41-1.38 (m 3H) ES-LCMS m/z 158 (M+H) .
92.4% at 0 - 25℃; for 12 h; Large scale To a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5:1, Rf= 0.6) showed the reaction wasfinished. The mixture was filtered, and most of the filtrate solvent was removed by reduced pressure. The mixture was quenched with water and extracted with EA, the organic layer was washed with brine, and then concentrated. Another six batches were34prepared following the same procedure to give 2-chloro-4-ethoxypyridine (1100 g, 7.01 mol, 92.4percent): ‘H NMR (400 MHz, CD3OD) 8.15 (d, J 6.0 Hz, 1H), 6.99 (d, J 2.0 Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H); ES-LCMS m/z: 158.1 (M+H).
92.4% at 0 - 25℃; for 12 h; Step 1 : 2-Chloro-4-ethoxypyridine To a mixture of 2-chloro-4-nitropyridine (170 g, 1070 mmol) in THF (2 L) was added sodium ethanolate (109.45 g, 1610 mmol) slowly at 0 °C. The mixture was stirred at 25 °C for 12 h. LCMS and TLC analysis (PE/EA = 5: 1, Rf = 0.6) showed the reaction was finished. The mixture was filtered, and most of the filtrate solvent was removed by reduced pressure. The mixture was quenched with water and extracted with EA, the organic layer was washed with brine, and then concentrated. Another six batches were prepared following the same procedure to give 2- chloro-4-ethoxypyridine (1100 g, 7.01 mol, 92.4percent): lH NMR (400 MHz, CD3OD) δ 8.15 (d, J = 6.0 Hz, 1H), 6.99 (d, J = 2.0 Hz, 1H), 6.91-6.89 (m, 1H), 4.16-4.14 (m, 2H), 1.41-1.38 (m, 3H); ES-LCMS m/z: 158.1 (M+H).
57% at 25℃; for 10 h; To a mixture of 2-chloro-4-nitropyridine (20 g, 126 mmol) in THF (200 mL) was added sodium ethoxide (25.8 g, 378 mmol) in portions. The mixture was stirred at 25 °C for 10 h. The mixture was filtered and the filtrate was concentrated. The crude material was purified by silica column chromatography (PE/EA = 5: 1). All fractions found to contain product by TLC (PE/EA = 5: 1, Rf = 0.6) were combined and concentrated to yield a light yellow solid of 2-chloro-4-ethoxypyridine (13 g, 71.9 mmol, 57percent yield): lH NMR (400 MHz, CDC13) δ 8.18 (d, J = 5.2 Hz, 1H), 6.82 (d, J = 2.4 Hz, 1H), 6.73 (dd, J = 2.0, 6.0 Hz, 1H), 4.09 (q, J =7.2 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H); ES- LCMS m/z 158 (M+H).

Reference: [1] Patent: WO2016/37578, 2016, A1, . Location in patent: Page/Page column 71; 72
[2] Patent: WO2016/38519, 2016, A1, . Location in patent: Page/Page column 34; 35
[3] Patent: WO2016/38552, 2016, A1, . Location in patent: Page/Page column 49
[4] Patent: WO2014/141187, 2014, A1, . Location in patent: Page/Page column 112; 52; 53
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
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Reference: [1] Patent: WO2014/137883, 2014, A1, . Location in patent: Page/Page column 37
  • 3
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YieldReaction ConditionsOperation in experiment
5 g Reflux 6.01.22.01 2-chloro-4-ethoxy-pyridine 33 ml sodium ethoxide was added to 19.2 g 2-chloro-4-iodopyridine in 150 mL ethanol. The reaction was refluxed overnight. Then water was added and extracted with tert-butyl- methylether. The organic layer was evaporated and the residue cleanded by chromatography on silica gel (petrolether/EtOAC:9/l) to yield 5 g of the desired compound. Rf: 0.3 (petrolether/EtOAC:4/l), (M+H)+: 158
5 g Reflux 6.01.22.01
2-chloro-4-ethoxy-pyridine
33 ml sodium ethoxide was added to 19.2 g 2-chloro-4-iodopyridine in 150 mL ethanol.
The reaction was refluxed overnight.
Then water was added and extracted with tert-butyl-methylether.
The organic layer was evaporated and the residue cleanded by chromatography on silica gel (petrolether/EtOAC:9/1) to yield 5 g of the desired compound.
Rf: 0.3 (petrolether/EtOAC:4/1), (M+H)+: 158
Reference: [1] Patent: WO2013/107761, 2013, A1, . Location in patent: Page/Page column 60; 61
[2] Patent: US2013/184248, 2013, A1, . Location in patent: Paragraph 0318; 0319; 0320
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
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