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[ CAS No. 25016-02-8 ]

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Chemical Structure| 25016-02-8
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CAS No. :25016-02-8 MDL No. :MFCD02093683
Formula : C8H7NO4 Boiling Point : 336.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :181.15 g/mol Pubchem ID :90685
Synonyms :

Safety of [ 25016-02-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25016-02-8 ]

  • Upstream synthesis route of [ 25016-02-8 ]
  • Downstream synthetic route of [ 25016-02-8 ]

[ 25016-02-8 ] Synthesis Path-Upstream   1~12

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Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6254 - 6276
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YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; 2-Hydroxy-5-nitrobenzaldehyde (1) (2 g, 12.0 mmol) was methylated using methyl iodide (1.7 g, 36 mmol) and anhydrous potassium carbonate (1.7 g, 36 mmol) in DMF (7 mL), by stirring at room temperature for 12 h. After the TLC showed complete disappearance of the starting material, the reaction mixture was poured in to crushed ice leading to the precipitation of the product. This was further purified by column chromatography over silica gel using 1:10 ethyl acetate/hexane to obtain a yield of 94percent (2.04 g) of compound (2). For characterization, the spectroscopic data was consistent with what has been previously reported (Yang et al., 2007, Org. Lett. 9:5287).1H NMR (CDCl3, 500 MHz): δ 10.48 (1H, s), 8.7 (1H, d, J=3.0 Hz), 8.47 (1H, dd, J=9 Hz), 7.05 (1H, d, 9 Hz), 4.04 (3H, s); 13C NMR (CDCl3, 100 MHz): 187.8, 165.8, 141.8, 130.9, 124.8, 112.5, 57.0.
87.8% With NaH In N,N-dimethyl-formamide Synthesis of 5-(N-methyl-N-methylsulfonylamino)-o-anisaldehyde
To a solution of 5-nitrosalicylaldehyde (1.00 g, 6.0 mmol) in DMF (20 ml) was added NaH (246 mg) and methyl iodide (2.56 g, 18 mmol) at 0° C.
The mixture was stirred for 8.5 hr at 60° C.
After the reaction mixture was extracted with ether, the extract was washed with aqueous NaHCO3, brine and 5percent-HCl/aq.NaCl, dried over MgSO4 and concentrated in vacuo to afford 2-methoxy-5-nitrobenzaldehyde (0.95 g, 87.8percent) as a yellow needle.
1 H NMR (CDCl3) δ: 10.45 (s, 1H), 8.70 (d, J=2.9 Hz, 1H), 8.45 (dd, J=8.8, 2.9 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 4.08 (s, 3H).
93.0% With sodium carbonate In <i>N</i>-methyl-acetamide Example 9
2-Methoxy-5-nitrobenzaldehyde
2-Hydroxy-5-nitrobenzaldehyde (2.40 g, 14.0 mmol) was dissolved in dimethylformamide (50 mL).
To this was added iodomethane (4.48 ml, 72.0 mmol) and sodium carbonate (3.04 g, 28.0 mmol).
This mixture was stirred for 24 hours and was poured into water.
The solid was collected by filtration to give 2.38 g (93.0percent).
Mp 88-89° C.;1 H NMR (CDCl3): d, 10.46 (s,1H), 8.69 (d,1H), 8.45 (dd,1H), 7.15 (d,1H), 4.10 (s,3H). MS (DCl): 182 (MH+). C8 H7 NO4.
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 15, p. 3435 - 3438
[2] Patent: US2013/261295, 2013, A1, . Location in patent: Paragraph 0166; 0167
[3] Journal of the American Chemical Society, 2017, vol. 139, # 19, p. 6654 - 6662
[4] Patent: US5837711, 1998, A,
[5] Journal of the Chemical Society, 1951, p. 2462,2466
[6] Patent: US5994563, 1999, A,
[7] Journal of the American Chemical Society, 2018,
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YieldReaction ConditionsOperation in experiment
62% at 0 - 20℃; for 3.08333 h; Inert atmosphere A solution of Intermediate 312A (520 mg, 2.92 mmol) in Et20 (23.400 mL) was cooled to 0 °C under an atmosphere of N2. A solution of DIBA1-H (1.0 M in Toluene) (4.38 mL, 4.38 mmol) was then added dropwise causing bubbling to occur. After 5 mmstirring, the reaction mixture was allowed to thaw to room temperature. After an additional 3 h, the orange solution was poured into a mixture of ice and 10 mL of glacialacetic acid. This mixture was stirred while the ice melted, diluted with EtOAc and DIwater and then extracted. The organic phase was concentrated and purified by ISCO(80g, 0-100percent EtOAc/Hexanes, 28 mm. Product at 55percent) to afford Intermediate 3 12B(410 mg, 1.811 mmol, 62.0 percent yield) as a light orange solid. LC-MS. Method H, RT =0.77 mm, MS (ESI) m/z: 182.1 (M+H). ‘HNMR (400MHz, CHLOROFORM-d)10.46 (s, 1H), 8.71 (d, J=2.9 Hz, 1H), 8.45 (dd, J=9.2, 2.9 Hz, 1H), 7.12 (d, J=9.2 Hz,1H), 4.08 (s, 3H).
Reference: [1] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 721
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Reference: [1] Patent: US4367234, 1983, A,
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Reference: [1] Synthetic Communications, 1982, vol. 12, # 4, p. 267 - 278
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 6, p. 1385 - 1392
[2] Chemische Berichte, 1882, vol. 15, p. 2025
[3] Chemische Berichte, 1884, vol. 17, p. 1387
[4] Chemische Berichte, 1882, vol. 15, p. 2025
[5] Chemische Berichte, 1884, vol. 17, p. 1387
[6] Journal of the Chemical Society [Section] C: Organic, 1971, p. 3693 - 3701
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Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1670 - 1674
[2] Canadian Journal of Chemistry, 1988, vol. 66, p. 1670 - 1674
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Reference: [1] Patent: WO2018/13774, 2018, A1,
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Reference: [1] Patent: US6369074, 2002, B1, . Location in patent: Example 19
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Reference: [1] Current Science, 1935, vol. 4, p. 26
[2] Current Science, 1935, vol. 4, p. 26
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Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 2445 - 2449
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YieldReaction ConditionsOperation in experiment
76% With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78 - 20℃; for 1 h; Inert atmosphere A solution of Intermediate 312B (410 mg, 2.263 mmol) in Toluene (11.500 mL) and THF (11.50 mL) was cooled to -78 °C under an atmosphere of N2. DIBAL-H (1.0 Min Toluene) (3.40 mL, 3.40 mmol) was then added to the cooled solution dropwise. After the initial bubbling had subsided, the reaction mixture was allowed to thaw to room temperature. After 1 h, the reaction mixture was cooled to 0 °C and quenched with 1.0 M HC1. The resulting suspension was stirred vigorously for 45 mm to fully cleave the aluminate complex. The mixture was then diluted with EtOAc and extracted. Theorganic phase was washed with brine, dried over MgSO4, filtered and concentrated. The resulting crude product was purified by ISCO (80g, 0-100percent EtOAc/Hexanes, 33 mm. Product at 50percent) to give Intermediate 312C (370 mg, 1.717 mmol, 76percent yield) as a light yellow solid. LC-MS. Method H, RT = 0.68 mm, MS (ESI) m/z: 184.0 (M+H). ‘H NMR (4001V11{z, CHLOROFORM-d) 8.29 (d, J=2.9 Hz, 1H), 8.21 (dd, J9.0, 2.6 Hz,1H), 6.94 (d, J=9.0 Hz, 1H), 4.75 (d, J=6.4 Hz, 2H), 3.97 (s, 3H), 2.07 (t, J=6.4 Hz, 1H).
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4638 - 4658
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6254 - 6276
[3] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 722
[4] Chemical Communications, 1998, # 22, p. 2443 - 2444
[5] Journal fuer Praktische Chemie (Leipzig), 1958, vol. &lt;4&gt; 6, p. 170,172
[6] Journal of Biological Chemistry, 1915, vol. 20, p. 674
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