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Chemical Structure| 129053-84-5

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Product Details of [ 129053-84-5 ]

CAS No. :129053-84-5
Formula : C8H10N2O3
M.W : 182.18
SMILES Code : O=C(O)CCNC(C1=CC=CN1)=O
MDL No. :MFCD08166665

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Application In Synthesis of [ 129053-84-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 129053-84-5 ]

[ 129053-84-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 129053-84-5 ]
  • [ 72908-87-3 ]
YieldReaction ConditionsOperation in experiment
54% at 80℃; General procedure: In methanesulfonic acid (13 mL, 195.8 mmol) was dissolved phosphorus pentoxide (2.02 g, 14.23 mmol) and heated to 80 °C. Once homogenous, carboxylic acid 7 (3.24 g, 17.78 mmol) was added, the reaction stirred and monitored by TLC until complete. The reaction was quenched with ice and exhaustively extracted with ethyl acetate. The combined organic extractions were dried (MgSO4) and concentration under vacuum to afford the desired product as a white solid (1.58 g, 54percent). mp = 280-282 °C; IR 3222, 2931, 1659, 1634 cm 1; 1H NMR δ 2.70 (2H, m), 3.35 (2H, m), 6.55 (1H, d, J = 2.7 Hz), 6.99 (1H, d, J = 2.7 Hz), 8.34 (1H, t, J = 4.7 Hz), 12.18 (1H, br s); 13C NMR δ 36.9, 43.8, 109.9, 122.7, 123.9, 128.3, 162.6, 194.7; LRMS (ES+) m/z 186.8 [M + Na]+; HRMS (ES+) 165.0657 ([M + H]+, 165.0664 calcd. for C8H9N2O2)
References: [1] Australian Journal of Chemistry, 1990, vol. 43, # 2, p. 355 - 365.
[2] Organic Letters, 2005, vol. 7, # 25, p. 5641 - 5644.
[3] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 2, p. 246 - 256.
[4] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 246 - 253,8.
[5] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 87 - 91.
[6] Tetrahedron Letters, 1995, vol. 36, # 3, p. 413 - 416.
[7] Tetrahedron, 2009, vol. 65, # 11, p. 2372 - 2376.
[8] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4306 - 4309.
[9] Patent: WO2008/147713, 2008, A1, . Location in patent: Page/Page column 34-35.
 

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