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Chemical Structure| 20357-24-8
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Product Details of [ 20357-24-8 ]

CAS No. :20357-24-8 MDL No. :MFCD00456498
Formula : C8H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :BNTDDWPHSMILHQ-UHFFFAOYSA-N
M.W : 181.15 Pubchem ID :230371
Synonyms :

Calculated chemistry of [ 20357-24-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.14
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 0.03
Log Po/w (SILICOS-IT) : -0.17
Consensus Log Po/w : 0.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.09 mg/ml ; 0.006 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.227 mg/ml ; 0.00125 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.85
Solubility : 2.54 mg/ml ; 0.014 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 20357-24-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20357-24-8 ]

* 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 [ 20357-24-8 ]
  • Downstream synthetic route of [ 20357-24-8 ]

[ 20357-24-8 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 20357-24-8 ]
  • [ 6705-03-9 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 2171
[2] Justus Liebigs Annalen der Chemie, 1912, vol. 391, p. 44
  • 2
  • [ 20357-24-8 ]
  • [ 55414-72-7 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6589 - 6592
  • 3
  • [ 20357-24-8 ]
  • [ 1882-69-5 ]
Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 2171
[2] Chemische Berichte, 1889, vol. 22, p. 2354
[3] Chemische Berichte, 1889, vol. 22, p. 2354
[4] Justus Liebigs Annalen der Chemie, 1912, vol. 391, p. 44
[5] Chemische Berichte, 1889, vol. 22, p. 2354
  • 4
  • [ 20357-24-8 ]
  • [ 1882-69-5 ]
  • [ 129841-08-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2007, vol. 128, # 12, p. 1461 - 1468
  • 5
  • [ 42454-06-8 ]
  • [ 74-88-4 ]
  • [ 20357-24-8 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16 h; Step 1.
Synthesis of 5-methoxy-2-nitrobenzaldehyde 2:
A mixture containing 5-hydroxy-2-nitrobenzaldehyde (1 eq) in DMF with iodomethane (1.1eq) and potassium carbonate (1eq) was stirred at room temperature for 16 hours.
The resulting mixture was concentrated and partitioned between ethyl acetate and water.
The organic layer was washed with brine and dried and concentrated to afford 5-methoxy-2-nitrobenzaldehyde in quantitative yield.
MS: MH+=182.
100% With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 10 h; Inert atmosphere 5-Hydroxy-2-nitrobenzaldehyde (25.0 g, 150 mmol) was dissolved in N,N- dimethylformamide (200 mL, 2000 mmol), followed by potassium carbonate (20.7 g, 150 mmol) and methyl iodide (10.2 mL, 164 mmol). The reaction mixture was stirred for 10 hours at 23 °C. Ethyl acetate (1000 mL) was added, and the mixture was washed with water and brine. Organic layer was dried over sodium sulfate. Removal of solvent gave a crude solid product, which was treated with DCM and hexanes. The solid was collected and washed with hexanes (27.Og, 100percent). 1H NMR (CHLOROFORM-d) δ: 10.50 (s, IH), 8.18 (d, J = 9.0 Hz, IH), 7.34 (d, J = 2.8 Hz, IH), 7.16 (dd, J = 9.2, 2.9 Hz, IH), 3.97 (s, 3H). MS (M+l): 182.10.
100% With potassium carbonate In N,N-dimethyl-formamide at 20℃; To a round bottom flask was added 5-hydroxy-2-nitrobenzaldehyde, 5 (15.6g, 93.3mmol) and DMF (200mL) followed by potassium carbonate (12.8g, 96.9mmol) and methyl iodide (5.35mL, 102.6mmol) and the mixture was stirred at RT overnight. The reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was dried with sodium sulfate and concentrated to obtain 16g of 5-methoxy-2-nitrobenzaldehyde in quantitative yield. To 5-methoxy-2-nitrobenzaldehyde (10.3g, 56.9mmol) in a round bottom flask was added ethylene glycol (4.49mL, 79.6mmol) and catalytic amounts of p-toluene sulfonic acid monohydrate (490mg) and toluene (100mL) and the flask was fitted with a Dean-Stark apparatus and the mixture was heated to 100oC overnight. The reaction mixture was filtered through a plug of celite and the filtrate was concentrated to obtain 14g of 2-(5-methoxy-2-nitrophenyl)-1, 3-dioxolane in 66.6percent yield. To 2-(5-methoxy-2-nitrophenyl)-1,3-dioxolane (14g, 62.2mmol) was added ethyl acetate (200mL) followed by sodium acetate (429mg) and catalytic amount of Platinum dioxide (840mg) and the mixture was hydrogenated at RT. The reaction mixture was then filtered through celite and the filtrate was concentrated to yield 12g of 2-(1, 3-dioxolan-2-yl)-4-methoxyaniline, 6 in 65.9percent yield. LC/MS m/z: 196.1 (MH+).
100% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8 h; In a 50 mL round bottom flask 0.668 g (4 mmol) was addedHydroxy-2-nitrobenzaldehyde, 400 μL (6 mmol)Of methyl iodide, 0.832 g (6 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide,The reaction was stirred at room temperature for 8h,After the reaction was completed, the reaction mixture was poured into an ice-water mixture,After the ice melted and extracted three times with dichloromethane, the organic phase was collected,Washed three times, saturated sodium bicarbonate solution and brine washed once with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the organic solvent to give a yellow solid as5-Methoxy-2-nitrobenzaldehyde (0.52 g, 100percent).
91%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere
Stage #2: Inert atmosphere
Example 348 : Synthesis of (1E,6E)-1-(4-hydroxyphenyl)-7-(5-methoxy-2-nitrophenyl)hepta-1,6-diene-3,5-dione (CU481); (1) Synthesis of 5-methoxy-2-nitrobenzaldehyde; To a solution of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (94 mg, 55percent, 2.1 mmol) under nitrogen at 0°C. After the solution was stirred at room temperature for 30 min, methyl iodide (0.17 mL, 2.7 mmol) was added with additional stirring for 30 min. The reaction mixture was quenched with saturated NH4Cl aqueous solution at 0°C, and the mixture was extracted with diethyl ether. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 80/20 to 70/30) to obtain the title compound as a pale yellow powder (298 mg, 91 percent).
91%
Stage #1: With sodium hydride In diphenylether at 0 - 20℃; Inert atmosphere
Stage #2: for 0.5 h;
To a solution of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (94 mg, 55percent, 2.1 mmol) under nitrogen at 0° C.
After the reaction mixture was stirred at room temperature for 30 min, methyl iodide (0.17 mL, 2.7 mmol) was added with additional stirring for 30 min.
After the reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C., the solution was extracted with ether.
The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4.
After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30) to obtain the title compound as a slightly yellow powder (298 mg, 91percent).
57% at 0℃; for 2 h; Inert atmosphere To a stirred suspension of NaH (60percent, 431 mg, 10.8 mmol) in dry DMF (30.0 mL) was added a solution of 3-hydroxy-6-nitrobenzaldehyde (Sigma-Aldrich, 1.50 g, 8.98 mmol) in dry DMF (10.0 mL) dropwise followed by MeI (671 μL, 10.8 mmol) at 0 °C under N2. The reaction mixture was stirred under N2 at 0 °C for 2 h, and concentrated in vacuo. The residue was partitioned between AcOEt and H2O. The organic extracts were washed with 2 N HCl, saturated aqueous NaHCO3, and brine, and concentrated in vacuo to afford 930 mg of the title product 28 in 57percent yield. 1H NMR (270 Hz, CDCl3) δ 10.48 (1H, s), 8.16 (1H, d, J = 9.1 Hz), 7.33 (1H, d, J = 2.8 Hz), 7.16 (1H, dd, J = 9.1 Hz, J = 2.8 Hz), 3.96 (3H, s).

Reference: [1] Patent: US2005/85482, 2005, A1, . Location in patent: Page/Page column 13; 17
[2] Patent: WO2010/51031, 2010, A1, . Location in patent: Page/Page column 45
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
[4] Patent: CN107522766, 2017, A, . Location in patent: Paragraph 0136; 0137; 0138
[5] Chemical Communications, 2011, vol. 47, # 42, p. 11683 - 11685
[6] Chemistry - A European Journal, 2004, vol. 10, # 10, p. 2487 - 2506
[7] Chemical Communications, 2011, vol. 47, # 10, p. 2802 - 2804
[8] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829
[9] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2408 - 2414
[10] Patent: EP2123637, 2009, A1, . Location in patent: Page/Page column 95
[11] Patent: US2011/82295, 2011, A1, . Location in patent: Page/Page column 10
[12] Journal of Fluorine Chemistry, 2007, vol. 128, # 12, p. 1461 - 1468
[13] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2250 - 2263
[14] Journal of the American Chemical Society, 2012, vol. 134, # 18, p. 7733 - 7740
[15] Tetrahedron, 2010, vol. 66, # 38, p. 7544 - 7561
[16] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 179 - 195
[17] Chemische Berichte, 1994, vol. 127, # 6, p. 1125 - 1130
[18] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1713 - 1716
[19] Patent: US5519133, 1996, A,
[20] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 771 - 774
[21] MedChemComm, 2016, vol. 7, # 4, p. 667 - 678
[22] Patent: WO2016/130968, 2016, A1, . Location in patent: Page/Page column 187
  • 6
  • [ 879-55-0 ]
  • [ 20357-24-8 ]
YieldReaction ConditionsOperation in experiment
100% With Dess-Martin periodane In dichloromethane at 20℃; for 3 h; To a solution of intermediate 37 (1.44 g, 7.9 mmol) in anh. CH2CI2 (40 mL) at r. t. , under N2, was added Dess-Martin periodinane (3.68 g, 1.1 eq). The reaction mixture was stirred for 3 HR AT r. t. , then sat. aq. Na2S203 (5 mL) and sat. aq. NaHCO3 (20 mL) were added. The phases were separated and the aqueous layer was extracted with EtOAc (2X100 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated to dryness to give 1.45 g (100percent) of the title compound. NMR (1H, CDCI3) : 8 10.47 (s, 1H), 8.14 (d, 1H), 7.31 (d, 1H), 7.13 (dd, 1H), 3.94 (s, 3H).
57% With dipyridinium dichromate In dichloromethane at 20℃; for 16 h; Example 8: 5-Methox -2-nitrobenzaldehydeTo the solution of (5-methoxy-2-nitrophenyl)methanol (18 g, 0.098 mol) in anhydrous DCM (0.2 L) was added PDC (11.5 g, 0.147 mol, 1.5 eq) and 4A MS (120 g) in portions. The mixture was stirred at room temperature for 16 h, filtered through a Celite pad. The filtrate was evaporated to dryness in vacuum to afford 5-methoxy-2- nitrobenzaldehyde (10 g, yield: 57percent) as a light yellow solid. 1HNMR (400 MHz, DMSO- d6) δ: 10.24 (s, 1H), 8.14 (d, / = 8.8 Hz, 1H), 7.31 (dd, / = 8.8, 3.2 Hz, 1H), 7.20 (d, J = 3.2 Hz, 1H), 3.89 (s, 3H); ESI-MS: m/z 182.0 ([M+l] +).
Reference: [1] Patent: WO2004/62665, 2004, A1, . Location in patent: Page/Page column 37
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2397 - 2407
[3] Patent: WO2012/109108, 2012, A1, . Location in patent: Page/Page column 39-40
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6412 - 6415
  • 7
  • [ 42454-06-8 ]
  • [ 77-78-1 ]
  • [ 20357-24-8 ]
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 5, p. 423 - 427
[2] Tetrahedron Letters, 1997, vol. 38, # 4, p. 533 - 536
[3] Journal of the Chemical Society, 1925, vol. 127, p. 1199
[4] Journal of the Chemical Society, 1925, vol. 127, p. 2171
  • 8
  • [ 42454-06-8 ]
  • [ 96042-30-7 ]
  • [ 74-88-4 ]
  • [ 20357-24-8 ]
Reference: [1] Patent: US2014/100195, 2014, A1, . Location in patent: Page/Page column
  • 9
  • [ 1882-69-5 ]
  • [ 20357-24-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6412 - 6415
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2397 - 2407
[3] Patent: WO2012/109108, 2012, A1,
  • 10
  • [ 100-83-4 ]
  • [ 20357-24-8 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2055
[2] Journal of the Chemical Society, 1925, vol. 127, p. 2171
[3] Tetrahedron, 2010, vol. 66, # 38, p. 7544 - 7561
  • 11
  • [ 63932-00-3 ]
  • [ 20357-24-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2397 - 2407
  • 12
  • [ 454466-57-0 ]
  • [ 20357-24-8 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 38, p. 7544 - 7561
  • 13
  • [ 109005-38-1 ]
  • [ 20357-24-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1991, # 6, p. 537 - 538
  • 14
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 2381
[2] Justus Liebigs Annalen der Chemie, 1912, vol. 388, p. 34
[3] Chemische Berichte, 1889, vol. 22, p. 2354
[4] Journal of the Chemical Society, 1926, p. 154[5] Journal of the Chemical Society, 1927, p. 2380
  • 15
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  • [ 20357-24-8 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2055
  • 16
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 134
[2] Journal of the Chemical Society, 1927, p. 2381
[3] Journal of the Chemical Society, 1926, p. 154[4] Journal of the Chemical Society, 1927, p. 2380
[5] Journal of the Chemical Society, 1932, p. 1112,1115
[6] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
  • 17
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 18
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 134
[2] Journal of the Chemical Society, 1927, p. 2381
[3] Journal of the Chemical Society, 1926, p. 154[4] Journal of the Chemical Society, 1927, p. 2380
[5] Journal of the Chemical Society, 1932, p. 1112,1115
[6] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 111, p. 230
  • 19
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 20
  • [ 20357-24-8 ]
  • [ 38469-84-0 ]
Reference: [1] Organic Preparations and Procedures International, 2009, vol. 41, # 5, p. 423 - 427
[2] Chemistry - A European Journal, 2004, vol. 10, # 10, p. 2487 - 2506
[3] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629
  • 21
  • [ 20357-24-8 ]
  • [ 7507-86-0 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6589 - 6592
  • 22
  • [ 20357-24-8 ]
  • [ 23842-82-2 ]
Reference: [1] Chemistry - A European Journal, 2004, vol. 10, # 10, p. 2487 - 2506
[2] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629
  • 23
  • [ 7697-37-2 ]
  • [ 591-31-1 ]
  • [ 20357-24-8 ]
  • [ 53055-05-3 ]
  • [ 80410-57-7 ]
Reference: [1] Patent: DE20116, , ,
[2] Chemische Berichte, 1889, vol. 22, p. 2341
[3] Chemische Berichte, 1885, vol. 18, p. 2572
[4] Chemische Berichte, 1889, vol. 22, p. 2354
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 586,587
  • 24
  • [ 20357-24-8 ]
  • [ 150192-39-5 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6589 - 6592
[2] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6589 - 6592
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