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[ CAS No. 66909-30-6 ]

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2D
Chemical Structure| 66909-30-6
Chemical Structure| 66909-30-6
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Product Details of [ 66909-30-6 ]

CAS No. :66909-30-6MDL No. :MFCD07375371
Formula : C7H6ClNO2 Boiling Point : 253°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :171.58Pubchem ID :12387730
Synonyms :

Computed Properties of [ 66909-30-6 ]

TPSA : 50.2 H-Bond Acceptor Count : 3
XLogP3 : 1.7 H-Bond Donor Count : 1
SP3 : 0.14 Rotatable Bond Count : 1

Safety of [ 66909-30-6 ]

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 [ 66909-30-6 ]

  • Upstream synthesis route of [ 66909-30-6 ]
  • Downstream synthetic route of [ 66909-30-6 ]

[ 66909-30-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 67-56-1 ]
  • [ 66909-30-6 ]
  • [ 65169-43-9 ]
Reference: [1] Patent: WO2007/41052, 2007, A2, . Location in patent: Page/Page column 78-79
  • 2
  • [ 65169-43-9 ]
  • [ 66909-30-6 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 2 h; INTERMEDIATE 322-Chloro-5-methylnicotinic acid; Intermediate 31 (0.38g, 1.81mmol) was dissolved in MeOH (2ml) and 2N NaOH solution was added (1.81ml, 3.62mmol) and the mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated to dryness and the residue redissolved in EtOAc/ <n="29"/>water. The organic layer was separated, dried over magnesium sulphate and concentrated in vacuum to yield the desired product as a white solid. Yield=94percent LRMS: m/z 172 (M+1 )+ Retention time: 3.25min 1H NMR (200 MHz, DMSO-D6) δ ppm: 2.2 (s, 3 H); 7.6 (d, 7=2.53 Hz, 1 H); 8.0 (d, J=2.53 Hz, 1 H)
Reference: [1] Patent: WO2008/77639, 2008, A1, . Location in patent: Page/Page column 26-27
  • 3
  • [ 124-38-9 ]
  • [ 66909-30-6 ]
Reference: [1] Patent: US2005/20611, 2005, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2007/41052, 2007, A2, . Location in patent: Page/Page column 78-79
  • 4
  • [ 124-38-9 ]
  • [ 66909-30-6 ]
Reference: [1] Patent: WO2007/108750, 2007, A1, . Location in patent: Page/Page column 78-79
  • 5
  • [ 18368-64-4 ]
  • [ 124-38-9 ]
  • [ 66909-30-6 ]
Reference: [1] Patent: WO2005/9965, 2005, A1, . Location in patent: Page/Page column 42
  • 6
  • [ 18368-64-4 ]
  • [ 66909-30-6 ]
Reference: [1] Patent: WO2007/108750, 2007, A1,
  • 7
  • [ 64-17-5 ]
  • [ 66909-30-6 ]
  • [ 894074-85-2 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5 h;
Stage #2: for 2 h;
Ethyl 2-chloro-5-methylnicotinate. To a solution of 2-chloro-5-methylnicotinic acid (3.90 g, 22.7 mmol) in DCM (100 ml_) was added oxalyl chloride (9.95 ml_, 1 14 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 ml_), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50percent DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82percent yield); 1 H NMR δ: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41-8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]
82%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5 h;
Stage #2: for 2 h;
To a solution of 2-chloro-5-methylnicotinic acid (3.90 g, 22.7 mmol) in DCM (100 mL) was added oxalyl chloride (9.95 mL, 114 mmol) followed by 1 drop of DMF. The resulting mixture was stirred at RT for 30 min and evaporated in vacuo. The residue thus obtained was taken up into EtOH (66 mL), stirred for a further 2 hr and then evaporated in vacuo. The crude product obtained was purified by flash column chromatography (S1O2, 120 g, 0-50percent DCM in isohexane, gradient elution) to afford the title compound as a colourless oil (3.71 g, 82percent yield); 1 H NMR δ: 1.32 (3H, t), 2.34 (3H, s), 4.34 (2H, q), 8.06-8.07 (1 H, m), 8.41 -8.43 (1 H, m). [See also: Yamamoto S. et al., Bioorg. Med. Chem. 2012, 20, 422-434.]
Reference: [1] Patent: WO2016/55791, 2016, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2017/175000, 2017, A1, . Location in patent: Page/Page column 28
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