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[ CAS No. 25391-57-5 ]

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2D
Chemical Structure| 25391-57-5
Chemical Structure| 25391-57-5
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Product Details of [ 25391-57-5 ]

CAS No. :25391-57-5MDL No. :MFCD04038464
Formula : C5H4IN3O2 Boiling Point : 365.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :265.01Pubchem ID :3384468
Synonyms :

Computed Properties of [ 25391-57-5 ]

TPSA : 84.7 H-Bond Acceptor Count : 4
XLogP3 : 1.5 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 25391-57-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25391-57-5 ]

  • Upstream synthesis route of [ 25391-57-5 ]
  • Downstream synthetic route of [ 25391-57-5 ]

[ 25391-57-5 ] Synthesis Path-Upstream   1~2

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YieldReaction ConditionsOperation in experiment
96%
Stage #1: With sulfuric acid; acetic acid; periodic acid In water at 90℃; for 0.166667 h;
Stage #2: With iodine In water for 60 h;
A 250 ml three-necked flask was charged with 2-amino-3-nitropyridine (10.0 g, 72.0 mmol),Acetic acid (44 mL) and water (10 mL).90 when addedPeriodic acid (3.28 g, 14.4 mmol)And the mass percentage concentration of 98percent concentrated sulfuric acid(1.3 mL); after stirring for 10 minutes, iodine (9.1 g, 36.0 mmol),Continue stirring at this temperature for 60 minutes. After cooling to room temperature,The reaction solution was added to a saturated aqueous solution of sodium thiosulfate (100 mL); separated by filtration,The solid was washed with saturated brine (50 mL x 2) and petroleum ether (50 mL x 2).The crude product was recrystallized from a mixture of petroleum ether and ethyl acetate (volume ratio: 5: 1)A yellow solid, high purity compound 1 (17.57 g, 69.1 mmol, 96percent) was obtained.
57%
Stage #1: at 90℃; for 0.25 h;
Stage #2: at 90℃; for 1 h;
a) 5-Iodo-3-nitropyridin-2-amineTo a solution of 3-nitropyridin-2-amine (1.2 g, 8.63 mmol) in acetic acid (5 ml), water (1 ml) and sulfuric acid (0.2 ml) was added periodic acid (0.4 g, 1.72 mmol, 0.2 eq.) and the mixture was stirred at 90 °C for 15 min. Iodine (0.87 g, 3.45 mmol, 0.4 eq.) was added portionwise and the mixture was heated at 90 °C for 1 h. The mixture was quenched by the addition of water and extracted with ethylacetate (3 χ 150 ml). The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate. The solvent was distilled off to give the product in 57 percent yield (1.3 g). 1H NMR (300 MHz, DMSO-< ): δ 8.58 (d, 1H), 8.54 (d, 1H) 8.04 (br s, 2H); LC-MS (ESI); Calculated mass: 265.01 : Observed mass: 265.9 [M+H]+ (rt: 1.36 min).
57%
Stage #1: With sulfuric acid; acetic acid; periodic acid In water at 90℃; for 0.25 h;
Stage #2: With iodine In water at 90℃; for 1 h;
To a solution of 3-nitropyridin-2-amine (1.2 g, 8.63 mmol) in acetic acid (5 ml), water (1 ml) and sulfuric acid (0.2 ml) was added periodic acid (0.4 g, 1.72 mmol, 0.2 eq.) and the mixture was stirred at 90° C. for 15 min.
Iodine (0.87 g, 3.45 mmol, 0.4 eq.) was added portionwise and the mixture was heated at 90° C. for 1 h.
The mixture was quenched by the addition of water and extracted with ethylacetate (3*150 ml).
The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate.
The solvent was distilled off to give the product in 57percent yield (1.3 g).
1H NMR (300 MHz, DMSO-d6): δ 8.58 (d, 1H), 8.54 (d, 1H) 8.04 (br s, 2H); LC-MS (ESI); Calculated mass: 265.01: Observed mass: 265.9 [M+H]+ (rt: 1.36 min).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[2] Patent: CN107325045, 2017, A, . Location in patent: Paragraph 0006; 0009
[3] Patent: WO2013/53983, 2013, A1, . Location in patent: Page/Page column 37
[4] Patent: US2015/11548, 2015, A1, . Location in patent: Paragraph 0152
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YieldReaction ConditionsOperation in experiment
79% With sulfuric acid; acetic acid In water 5-Iodo-3-nitro-2-aminopyridine
A mixture of 2-amino-3-nitropyridine (5.0 g, 35.9 mmol), acetic acid (22 mL), water (5 mL), sulfuric acid (0.650 mL), and HIO4*2H2O (1.7 g, 7.5 mmol) was allowed to stir at 90° C. for 10 min.
Iodine crystals (3.7 g, 14.6 mmol) were added in portions.
After stirring for 1 h, the reaction was poured into saturated sodium thiosulfate and extracted with ethyl acetate.
The organic layers were washed with 0.1 M NaOH and saturated brine, dried with sodium sulfate, then evaporated to give orange solid (7.5 g, 79percent yield).
mp 213-215° C.; 1H NMR (DMSO) δ (ppm) 8.03 (br s, 2H), 8.53 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H); 13C NMR (DMSO) δ (ppm) 74.18, 127.92, 141.31, 152.50, 160.88.
Analytical Calculated for C5H4O2N3I: C, 22.66; H, 1.52; N, 15.86; Found: C, 22.88; H, 1.53; N, 15.69.
Reference: [1] Patent: US6538010, 2003, B1,
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