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Chemical Structure| 14150-94-8
Chemical Structure| 14150-94-8
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Product Details of [ 14150-94-8 ]

CAS No. :14150-94-8 MDL No. :MFCD00456280
Formula : C6H5N3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :QARVELJVEBLWGK-UHFFFAOYSA-N
M.W : 199.12 Pubchem ID :3621236
Synonyms :

Safety of [ 14150-94-8 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P280-P370+P378 UN#:1325
Hazard Statements:H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14150-94-8 ]

* 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 [ 14150-94-8 ]
  • Downstream synthetic route of [ 14150-94-8 ]

[ 14150-94-8 ] Synthesis Path-Upstream   1~22

  • 1
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 2
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YieldReaction ConditionsOperation in experiment
30% at 100℃; To a stirred mixture of 1-METHYL-LH-PYRIDIN-2-ONE (33.47 g, 0.306 mol) and concentrated H2S04 (300 ML) at 100 °C was added concentrated HNO3 (120 mL) in portions. The reaction mixture was heated at this temperature overnight, and then poured into ice (1400 mL). The precipitate was filtered off and washed with water to give the title compound (Yield: 18.66 g, 30percent). LH NMR (400 MHZ, CDCl3) : 8 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H).
28% at 0 - 100℃; for 5 h; 1-Methyl-2-pyridone (25.0 g, 0.229 mol) was added to sulfuric acid (500 mL) at 0° C.
After stirring for 5 min., nitric acid (200 mL) was added dropwise at 0° C.
After addition, the reaction temperature was slowly raised to 100° C., and then maintained for 5 h.
The reaction mixture was poured into ice, basified with potassium carbonate to pH 8 and extracted with CH2Cl2 (100 mL*3).
The combined organic layers were dried over Na2SO4 and concentrated to yield 1-methyl-3,5-dinitro-2-pyridone (12.5 g, 28percent), which was used without further purification.
22% at 100℃; for 4 h; Step 1: To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60 percent) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100 °C for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22 percent)
22% at 20 - 100℃; To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60percent) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100° C. for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22percent)

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5392 - 5397
[2] Patent: WO2004/69832, 2004, A2, . Location in patent: Page 137-138
[3] Patent: US2011/98311, 2011, A1,
[4] Patent: US2012/309758, 2012, A1,
[5] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0698
[6] Patent: WO2013/13816, 2013, A1, . Location in patent: Page/Page column 71; 72
[7] Patent: US2013/29995, 2013, A1, . Location in patent: Paragraph 0360-0361
[8] Patent: WO2007/48070, 2007, A2, . Location in patent: Page/Page column 106
  • 3
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Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 7, p. 2171 - 2172
  • 4
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Reference: [1] Patent: US2015/231142, 2015, A1,
  • 5
  • [ 2459-07-6 ]
  • [ 77-78-1 ]
  • [ 14150-94-8 ]
  • [ 139004-71-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 8, p. 2176 - 2186
  • 6
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
  • 7
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
  • 8
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
  • 9
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
  • 10
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
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Reference: [1] Journal of the Chemical Society, 1951, p. 2590,2593
  • 14
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 15
  • [ 14150-94-8 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 16
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 17
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180
  • 18
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  • [ 96-22-0 ]
  • [ 16947-63-0 ]
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 6, p. 1203 - 1206
[2] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2820 - 2827
  • 19
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8856 - 8858
[2] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2820 - 2827
  • 20
  • [ 14150-94-8 ]
  • [ 120-92-3 ]
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YieldReaction ConditionsOperation in experiment
87% With ammonium acetate In ethanol at 65℃; for 2 h; Microwave irradiation General procedure: To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in EtOH (5 mL), cyclohexanone 4a (26 μL, 0.25 mmol) and NH4OAc (289 mg, 3.75 mmol) were added, and the resultant mixture was heated at 65 °C on an oil bath for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to afford 5,6,7,8-tetrahydro-3-nitroquinoline (5a; 42 mg, 0.24 mmol, 95percent) as a yellow powder. The reactions of dinitropyridone 1 with other ketones 4b–g were performed in a similar way. When the reaction was conducted using microwave heating, the procedure was analogous.
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 16, p. 2175 - 2178
[2] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2820 - 2827
  • 21
  • [ 14150-94-8 ]
  • [ 108-94-1 ]
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YieldReaction ConditionsOperation in experiment
44% With ammonia In methanol at 70℃; for 3 h; Inert atmosphere A mixture of 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (947 mg, 4.76 mmol), cyclohexanone (0.5 mL, 5.70 mmol) and ammonia solution (1 M) in methanol (50 mL) was heated to 70 °C for 3 h under N2. TLC showed complete consumption of starting material. The reaction mixture was removed in vacuo and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford 3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (C). (340 mg, 44 percent)
Reference: [1] Patent: WO2013/13816, 2013, A1, . Location in patent: Page/Page column 72
  • 22
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Reference: [1] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2820 - 2827
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