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[ CAS No. 77156-85-5 ]

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2D
Chemical Structure| 77156-85-5
Chemical Structure| 77156-85-5
Structure of 77156-85-5 *Storage: {[proInfo.prStorage]}

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Product Details of [ 77156-85-5 ]

CAS No. :77156-85-5MDL No. :MFCD02217815
Formula : C13H12ClNO3 Boiling Point : 366.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :265.69Pubchem ID :728976
Synonyms :

Computed Properties of [ 77156-85-5 ]

TPSA : 48.4 H-Bond Acceptor Count : 4
XLogP3 : 3 H-Bond Donor Count : 0
SP3 : 0.23 Rotatable Bond Count : 4

Safety of [ 77156-85-5 ]

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 [ 77156-85-5 ]

  • Upstream synthesis route of [ 77156-85-5 ]
  • Downstream synthetic route of [ 77156-85-5 ]

[ 77156-85-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 63463-15-0 ]
  • [ 77156-85-5 ]
YieldReaction ConditionsOperation in experiment
92% With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 65℃; for 2.5 h; Step C.
Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate.
To a solution of ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate (2.72 g, 11.0 mmol) in chloroform (100 mL) was added oxalyl chloride (2.93 mL, 33.0 mmol) followed by 5 drops of DMF.
The reaction was heated at 65° C. for 2.5 h before cooling to ambient temperature.
The reaction mixture was poured into saturated NaHCO3 (aq.) solution and the organics were extracted with DCM.
The combined organics were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound as a yellow solid (2.69 g, 92percent).
1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H), 8.33 (d, J=9.4 Hz, 1H), 7.58 (br. s., 1H), 7.37 (d, J=9.0 Hz, 1H), 4.48 (q, J=6.8 Hz, 2H), 4.01 (s, 3H), 1.45 (t, J=7.0 Hz, 3H).
[M+H]=266.2.
91% With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 35 - 40℃; for 2.5 h; A mixture of ethyl-4-hydroxy-7-methoxyquinoline-3-carboxylate DK-I-39-1 (37.1 g, 150.0 mmol), N,N- dimethylformamide (0.5 mL, 6.5 mmol), and dichloromethane (150 mL) was heated to 35-40 oC. Oxalyl chloride (20.9 g, 165.0 mmol) was added dropwise to the reaction mixture over 30 min. The reaction mixture was then heated for 2 h at reflux (38-40 oC). The resulting brown solution was then cooled to 20-25 oC. The reaction mixture was diluted with dichloromethane (150 mL) and then neutralized by slowly adding a 25percent solution of potassium carbonate (75 g) in water (300 mL). The layers were then separated and the aqueous layers extracted with dichloromethane (100 mL). The combined organic layers were then washed with a 25percent solution of potassium carbonate (75 g) in water (300 mL). The combined organic layers were then dried over magnesium sulfate. The solvents were then removed by evaporation on a rotovap and the product residue was slurried with hexanes (200 mL). The solid product was then filtered and washed twice with hexanes (50 mL x 2). The solid was dried to afford the product as an off-white solid DK-I-40-1 (36.3 g, 91percent): 1H NMR (300 MHz, DMSO) δ 9.08 (s, 1H), 8.25 (d, J = 9.2 Hz, 1H), 7.57– 7.37 (m, 2H), 4.41 (q, J = 7.1 Hz, 2H), 3.98 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H); 13C NMR (75 MHz, DMSO) δ 164.32, 162.83, 151.62, 150.81, 142.02, 126.85, 122.12, 121.11, 120.56, 108.36, 62.15, 56.45, 14.49; HRMS m/z calculated for C13H13ClNO3 (M+H)+ 266.0584 found 266.15.
68% at 140℃; for 1 h; Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate (0.68 g, 2.75 mmol) was added tophosphorus oxychloride (2 mL) and heated at 140 oc for an hour. The mixture was thenpoured onto ice, neutralized with 1M NaOH resulting in a solid that was filtered, washed withwater and dried to afforded product (0.50 g, 68percent) as yellowish solid. OH (400 MHz; CDCb)1.46 (3H, t, J =4.0 Hz), 3.99 (3H, s), 4.48 (2H, q, J =8.0 Hz), 7.33(1H, m), 7.44 (1H, d, J=2.8 Hz), 8.30 (1H, d, J= 8.0 Hz), 9.17 (1H, s). 8c (100 MHz; CDCb) 14.2, 55.8, 61.8, 107.6,120.7, 121.5, 126.7, 143.4, 150.9, 151.7.
Reference: [1] Patent: US2014/275548, 2014, A1, . Location in patent: Paragraph 0361
[2] Patent: WO2016/196961, 2016, A1, . Location in patent: Paragraph 00149
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2422 - 2446
[4] Patent: WO2018/129274, 2018, A1, . Location in patent: Paragraph 0046
[5] Farmaco, 1998, vol. 53, # 8-9, p. 579 - 585
[6] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1669 - 1673
[7] Patent: WO2006/14618, 2006, A2, . Location in patent: Page/Page column 37-38
  • 2
  • [ 71083-05-1 ]
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YieldReaction ConditionsOperation in experiment
36% at 115℃; for 0.75 h; Description 106; Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate; A suspension of Description 105 (28. 6 g, 0.12 mol) in POCl3 (34 ml, 0.36 moD was heated at 115°C for 45mins. The cooled reaction mixture was poured onto ice (500 ml) and cooled in an ice bath. 33percent aqueous ammonia was added until a pH of 7 was obtained (80-90 ml). The solid which formed was collected by filtration. Ether was added to the solid, the mixture stirred then filtered. This procedure was repeated 4 times and the combined ether extracts were evaporated to give a yellow solid (ll. lg, 36percent). 1H NMR (400 MHz, DMSO-d6) 1.38 (3 H, t, J7. 1), 3.99 (3 H, s), 4.41 (2 H, q, J7.1), 7.48 (1 H, dd, J9. 3 and 2. 6), 7.53 (1 H, d, J2.5), 8. 28 (lH, d, J9.2), 9.10 (1 H, s).
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2756 - 2766
[2] Patent: WO2005/47279, 2005, A1, . Location in patent: Page/Page column 54
[3] Patent: EP1154774, 2005, B1, . Location in patent: Page/Page column 116-117
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4205 - 4219
  • 3
  • [ 536-90-3 ]
  • [ 77156-85-5 ]
Reference: [1] Farmaco, 1998, vol. 53, # 8-9, p. 579 - 585
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1669 - 1673
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4205 - 4219
[4] Patent: US2014/275548, 2014, A1,
[5] Patent: WO2018/129274, 2018, A1,
  • 4
  • [ 87-13-8 ]
  • [ 77156-85-5 ]
Reference: [1] Farmaco, 1998, vol. 53, # 8-9, p. 579 - 585
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1669 - 1673
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4205 - 4219
[4] Patent: US2014/275548, 2014, A1,
[5] Patent: WO2018/129274, 2018, A1,
  • 5
  • [ 56881-19-7 ]
  • [ 77156-85-5 ]
Reference: [1] Farmaco, 1998, vol. 53, # 8-9, p. 579 - 585
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4205 - 4219
[3] Patent: US2014/275548, 2014, A1,
[4] Patent: WO2018/129274, 2018, A1,
  • 6
  • [ 536-90-3 ]
  • [ 87-13-8 ]
  • [ 77156-85-5 ]
Reference: [1] Patent: WO2016/196961, 2016, A1,
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2422 - 2446
  • 7
  • [ 77156-85-5 ]
  • [ 852062-08-9 ]
YieldReaction ConditionsOperation in experiment
89% at 20℃; for 72 h; Description 107; 4-Chloro-7-methoxyquinoline-3-carboxylic acid; To a stirring suspension of Description 106 (11.1 g, 41 mmol) in ethanol (100 ml) was added 2M NaOH (100ml). The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water (100 mD, cooled in an ice/water bath and acidified to pH 4 by addition of conc. HCl. The resulting solid was collected by filtration, washed with water and dried under vacuum in a drying pistol at 50°C (8. 8 g, 89percent). 1H NMR (400 MHz, DMSO-d6) 3.98 (3 H, s), 7. 48 (1H, dd, J9.2 and 2.5), 7.52 (1 H, d', J2. 5), 8. 28 (1 H, d, J 9.2), 9.11 (1 H, s).
Reference: [1] Patent: WO2005/47279, 2005, A1, . Location in patent: Page/Page column 54
  • 8
  • [ 77156-85-5 ]
  • [ 659730-27-5 ]
Reference: [1] Patent: US2014/275548, 2014, A1,
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