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Chemical Structure| 7579-20-6

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Product Details of 3-Aminoisonicotinic acid

CAS No. :7579-20-6
Formula : C6H6N2O2
M.W : 138.12
SMILES Code : O=C(O)C1=CC=NC=C1N
MDL No. :MFCD00137840
InChI Key :FYEQKMAVRYRMBL-UHFFFAOYSA-N
Pubchem ID :459531

Safety of 3-Aminoisonicotinic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Aminoisonicotinic acid

* 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 [ 7579-20-6 ]
  • Downstream synthetic route of [ 7579-20-6 ]

[ 7579-20-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 64-17-5 ]
  • [ 7579-20-6 ]
  • [ 14208-83-4 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: for 20 h; Heating / reflux
Stage #2: With sodium hydroxide In water
To an ethanol (20mL) solution of 3-aminolsonicotinoic acid (1.4g, 10 mmol), conc. sulfuric acid (2.94g, 30 mmol) was added and refluxed under heating for 20 hours.
The reaction liquid was distilled under reduced pressure.
Water was added to the obtained residue, which was made its pH to 8-9 with a 2N sodium hydroxide solution under ice-cooling.
The precipitated solid was filtered and dried to give ethyl 3-aminoisonicotinate (0.70g, 42percent).
Further, the filtrate was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, subsequently, and dried over anhydrous magnesium sulfate.
The solvent was distilled under reduced pressure to give ethyl 3-aminoisonicotinoate (0.30g, 18percent)
1H-NMR (DMSO-d6) δ:1.30(3H,t,J=7.1Hz), 4.28(2H,q,J=7.1Hz), 6.66 (2H,br.s), 7.45(1H,d,J=5.2Hz), 7.73(1H,d,J=5.2Hz), 8.23(1H,s)
References: [1] Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 987 - 993.
[2] Patent: EP1844768, 2007, A1, . Location in patent: Page/Page column 29-30.
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 547,553.
[4] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84.
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2676 - 2688.
[6] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071.
[7] Patent: WO2011/150156, 2011, A2, . Location in patent: Page/Page column 128.
  • 2
  • [ 7579-20-6 ]
  • [ 14208-83-4 ]
References: [1] Patent: US5250548, 1993, A, .
  • 3
  • [ 7579-20-6 ]
  • [ 58484-01-8 ]
References: [1] Patent: WO2008/130021, 2008, A2, .
  • 4
  • [ 7579-20-6 ]
  • [ 53975-70-5 ]
References: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387.
 

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