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[ CAS No. 874493-25-1 ] {[proInfo.proName]}

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Chemical Structure| 874493-25-1
Chemical Structure| 874493-25-1
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CAS No. :874493-25-1 MDL No. :MFCD09839283
Formula : C6H5BrN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :TZYNRASKYAQOML-UHFFFAOYSA-N
M.W : 233.02 Pubchem ID :29919394
Synonyms :

Safety of [ 874493-25-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 874493-25-1 ]

* 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 [ 874493-25-1 ]

[ 874493-25-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 874493-25-1 ]
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YieldReaction ConditionsOperation in experiment
81.4% at 80℃; 3-Bromo-6-methyl-5-nitropyridin-2-ol (9.2 g, 36.7 mmol) in POCl3 (56.2 g, 366.7 mmol) was stirred at 80° C. overnight.
The mixture was slowly poured into water (800 mL) and a solid was formed.
The solid was collected and dried to afford the desired product (7.5 g, 81.4percent yield).
65% for 7 h; Reflux Preparation 13D: 3 -bromo-2-chloro-6-methyl-5 -nitropyridine [00276j In a 500-mL single round-bottomed flask, POC13 (12 g, 78.1 mmol) was added dropwise to 3-bromo-6-methyl-5-nitropyridin-2-ol (4 g, 15.87 mmol). This mixture was then stirred at reflux for 7 h. The reaction mixture was cooled to 30 °C, poured into ice water and stirred for 10 mm. Saturated NaHCO3 solution (30 mL) was then added. The aqueous layer was extracted with EtOAc (200 mL x 3). The combined organic layers were washed with water, brine (200 mL x 2), dried over Na2504, filtered and concentrated to give 2.8 g (65 percent) of the title compound as a yellow solid. ‘H NMR (400 MHz, CDC13) ? 8.55 (s, 1 H), 2.83 (s, 3 H).
65% for 7 h; Reflux In a 500-mL single round-bottomed flask, POCI3 (12 g, 78.1 mmol) was added dropwise to 3-bromo-6-methyl-5-nitropyridin-2-ol (4 g, 15.87 mmol). This mixture was then stirred at reflux for 7 h. The reaction mixture was cooled to 30 °C, poured into ice water and stirred for 10 min. Saturated NaHC03 solution (30 mL) was then added. The aqueous layer was extracted with EtOAc (200 mL x 3). The combined organic layers were washed with water, brine (200 mL x 2), dried over Na2S04, filtered and concentrated to give 2.8 g (65 percent) of the title compound as a yellow solid. 1H NMR (400 MHz, CDC13) δ 8.55 (s, 1 H), 2.83 (s, 3 H).
Reference： [1] Patent: US2018/170909, 2018, A1, . Location in patent: Paragraph 1925; 1926
[2] Patent: WO2015/89192, 2015, A1, . Location in patent: Paragraph 00275; 00276
[3] Patent: WO2016/37005, 2016, A1, . Location in patent: Paragraph 00259-00260
[4] Patent: WO2008/101682, 2008, A2, . Location in patent: Page/Page column 42-43
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Reference： [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
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