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[ CAS No. 908248-27-1 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 908248-27-1
Chemical Structure| 908248-27-1
Structure of 908248-27-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 908248-27-1 ]

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Product Details of [ 908248-27-1 ]

CAS No. :908248-27-1MDL No. :MFCD13193356
Formula : C5H5N3O3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :155.11Pubchem ID :5373425
Synonyms :

Computed Properties of [ 908248-27-1 ]

TPSA : 105 H-Bond Acceptor Count : 5
XLogP3 : 0 H-Bond Donor Count : 2
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 908248-27-1 ]

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

Application In Synthesis of [ 908248-27-1 ]

  • Upstream synthesis route of [ 908248-27-1 ]
  • Downstream synthetic route of [ 908248-27-1 ]

[ 908248-27-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 21594-54-7 ]
  • [ 908248-27-1 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With sodium hydroxide; water In ethanol at 80℃; for 3.00 h;
Stage #2: With hydrogenchloride; sodium carbonate In ethanol; water
A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6- nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 °C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.
86%
Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 3.00 h;
Stage #2: With hydrogenchloride In ethanol; water
Stage #3: With sodium carbonate In ethanol; water
3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 0C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pΗ adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.
86%
Stage #1: With water; sodium hydroxide In ethanol at 80℃; for 3.00 h;
Stage #2: With hydrogenchloride In ethanol; water
Stage #3: With sodium carbonate In ethanol; water
3. Synthesis of 2-amino-5-nitropyridin-3-ol.A solution of sodium hydroxide (500 mmol) in water (180 ml) was added to a solution of 6-nitrooxazolo[4,5-b]pyridin-2(3H)-one (124 mmol) in ethanol (100 ml) and the reaction mixture was heated at 80 0C for 3 h. The reaction mixture was quenched with concentrated hydrochloric acid (40 mL) and the pH adjusted to 8 with 2 M sodium carbonate. The precipitated solids were collected by filtration to provide 2-amino-5-nitropyridin-3-ol in 86percent yield as a yellow solid.
39% With sodium hydroxide In ethanol; water at 80℃; for 3.00 h; Into a 500-mL round-bottom flask, was placed a solution of 6-nitro-2H,3H-[1,3]oxazolo[4,5-b]pyridin-2-one (30 g, 165.65 mmol, 1.00 equiv) in ethanol (130 mL).
Then a solution of sodium hydroxide (24 g, 600.00 mmol, 3.62 equiv) in water (225 mL) was added.
The resulting solution was stirred for 3 h at 80° C.
The reaction was then quenched by the addition of 48 mL of concentrated hydrochloric.
The pH value of the solution was adjusted to 8 with 2M sodium carbonate.
The solids were collected by filtration.
This resulted in 10 g (39percent) of 2-amino-5-nitropyridin-3-ol (I-12) as a yellow solid.
37% With water; sodium hydroxide In tetrahydrofuran at 85℃; for 2.00 h; 10percent Aqueous sodium hydroxide solution (44.40 mmol, 17.8 mL) was added to a suspension of 6-nitrooxazolo [ 4 , 5- b]pyridin-2 (3H) -one (11.10 mmol, 2 .00 g) in THF (10 mL) . The mixture was heated at 85°C for 2 hours. The mixture was cooled (ice/water bath) then acidified to pH6 (0774) (concentrated hydrochloric acid) . The resulting (0775) precipitate was isolated by filtration, washed with water then dried under suction to give the title compound as an orange powder (4.30 g, 37percent).

Reference: [1] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 120-121
[2] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 85
[3] Patent: WO2010/24980, 2010, A1. Location in patent: Page/Page column 103; 104
[4] Patent: US2014/274926, 2014, A1. Location in patent: Paragraph 0529; 0530
[5] Patent: WO2015/115673, 2015, A1. Location in patent: Page/Page column 76-77
  • 2
  • [ 896161-12-9 ]
  • [ 908248-27-1 ]
YieldReaction ConditionsOperation in experiment
49% at 150℃; for 3.00 h; 2-amino-3-hydroxy-5-nitropyridine
Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol).
The solid mixture was heated at 150° C. (upon which the solids fused; the evolution of a gas was also apparent).
The mixture was held at 150° C. for three hours upon which reaction was deemed complete by LC-MS.
After allowing to cool to 80° C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3*100 ml).
The combined organic extracts were washed with water (2*100 mL), dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue.
The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10percent) gradient as eluent to give the product as a solid (0.138 g, 49 percent) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).
49% at 150℃; for 3.00 h; 2-amino-3-hydroxy-5-nitropyridine; Into a 500 mL round bottom flask were combined 2-amino-3-methoxy-5-nitropyridine (0.300 g, 0.00177 mol) and solid pyridine hydrochloride (8.8 g, 0.076 mol). The solid mixture was heated at 150° C. upon which the solids fused (the evolution of a gas was also apparent). The mixture was held at 150° C. for three hours upon which reaction was deemed complete by LC-MS. After allowing to cool to 80° C., the mixture was poured on to ice and the aqueous layer was extracted with ethyl acetate (3.x.100 ml). The combined organic extracts were washed with water (2.x.100 mL), dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using a methanol:methylene chloride (0-10percent) gradient as eluent to give the product as a solid (0.138 g, 49percent) which was used directly in the next step. LC-MS 1.28 min. m/z=155.9 (M+1).
Reference: [1] Patent: US2006/194801, 2006, A1. Location in patent: Page/Page column 55
[2] Patent: US2006/205773, 2006, A1. Location in patent: Page/Page column 32
  • 3
  • [ 16867-03-1 ]
  • [ 908248-27-1 ]
Reference: [1] Patent: US2014/274926, 2014, A1
[2] Patent: WO2015/115673, 2015, A1
  • 4
  • [ 60832-72-6 ]
  • [ 908248-27-1 ]
Reference: [1] Patent: US2014/274926, 2014, A1
[2] Patent: WO2015/115673, 2015, A1
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