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[ CAS No. 57179-35-8 ]

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Chemical Structure| 57179-35-8
Chemical Structure| 57179-35-8
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CAS No. :57179-35-8 MDL No. :MFCD16998726
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :152.15 g/mol Pubchem ID :5314561
Synonyms :

Safety of [ 57179-35-8 ]

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 [ 57179-35-8 ]

  • Upstream synthesis route of [ 57179-35-8 ]
  • Downstream synthetic route of [ 57179-35-8 ]

[ 57179-35-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 7311-34-4 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
88% With formaldehyd; sodium thioethylate In N,N-dimethyl-formamide at 145℃; for 1 h; To a 1.0-L three-neck flask was added sodium ethanethiolate (80percent, 28.5 g, 271.0 mmol) and anhydrous DMF (225 mL). The mixture was heated to 145° C. for 1.5 hours. Then, 3,5-dimethoxy-benzaldehyde (15.0 g, 90.0 mmol) in anhydrous DMF (350 mL) was added over a period of 8 minutes. The reaction was kept at 145° C. for another 1 hour, then cooled to room temperature. Saturated sodium chloride solution (2.5 L) and formaline (37percent, 240 mL) together with acetic acid (500 mL) was added. The resulting solution was thoroughly extracted with ethyl acetate, the organic phase was dried with sodium sulfate, and the solvent was removed under vacuum. The crude compound was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1) to give 3-hydroxy-5-methoxy-benzaldehyde as a white solid. Yield: 12.0 g (88percent)
70% With sodium hydride In N,N-dimethyl-formamide; ethanethiol; mineral oil for 1 h; Inert atmosphere; Reflux NaH (2.72 g, 71.4 mmol, 60percent in mineral oil) was taken in an oven-dried RB flask equipped with magnetic stir bar and anhydrous DMF (60 mL) was added. After cooling the solution at 0° C., ethanethiol (7 mL, 93.4 mmol) was slowly added via a syringe, once the evolution of H2 ceased, it was refluxed under N2 atmosphere for 1 h. Next, aldehyde E (3.84 g, 23.6 mmol) in DMF (90 mL) was added and the resulting solution was refluxed under N2 atmosphere for 1 h. The reaction mixture was then cooled and quenched by the addition of saturated aqueous NaCl (750 mL), 26percent formaline (75 mL), and acetic acid (140 mL). The reaction mixture was then thoroughly extracted with ethyl acetate, the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain a crude dark syrup. The crude syrup was purified by gradient column chromatography using hexanes and ethyl acetate (100:1 to 1:1) to afford the desired aldehyde F as a yellow solid (70percent). [0099] 1H NMR (500 MHz, CDCl3): δ 9.84 (s, 1H, —CHO), 6.96 (d, J=2.5 Hz, 2H), 6.68 (t, J=2.1 Hz, 1H), 3.83 (s, 3H). [0100] 13C NMR (125 MHz, CDCl3): δ 192.8, 161.2, 158.6, 138.1, 109.2, 108.2, 106.0, 55.4
17.6% With sodium hydride; ethanethiol In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.5 h; Heating / reflux Example 16-1
Preparation for 3-hydroxy-5-methoxybenzaldehyde
To a solution of 60percent sodium hydride (2.77g, 69.3mmol) in N,N-dimethylformamide (50ml) was gradually added at 0°C ethanethiol (7ml), and the solution was stirred at 0°C for 30 minutes, followed by refluxing under heating for 1 hour..
The mixture was cooled to room temperature, and thereto was added 3,5-dimethoxybenzaldehyde (3.84g, 23.1mmol) in N,N-dimethylformamide (90ml) and the mixture was refluxed under heating for 1 hour..
The mixture was cooled to room temperature, and thereto were added a saturated aqueous sodium chloride solution (700ml), 26percent aqueous formalin solution (70ml) and acetic acid (130ml) in the order..
The mixture was stirred, extracted with ethyl acetate..
The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate..
The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography (hexane:ethyl acetate=2:1) to give the subject compound (2.68g, 17.6percent).1H NMR (CDCl3, 400 MHz) δ 9.88 (s, 1 H), 7.00 (m, 1 H), 6.96 (m, 1 H), 6.68 (t, 1 H, J = 2.3 Hz), 3.84 (s, 3 H).
Reference: [1] Patent: US2013/281399, 2013, A1, . Location in patent: Paragraph 0791; 0797
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 40, p. 5605 - 5614
[3] Journal of Organic Chemistry, 1985, vol. 50, # 13, p. 2236 - 2240
[4] Patent: US2014/309427, 2014, A1, . Location in patent: Paragraph 0097; 0098; 0099; 0100
[5] PLoS ONE, 2015, vol. 10, # 10,
[6] Patent: EP1386913, 2004, A1, . Location in patent: Page 65-66
[7] Patent: WO2016/14529, 2016, A1, . Location in patent: Page/Page column 25
  • 2
  • [ 26153-38-8 ]
  • [ 74-88-4 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
39% With potassium carbonate In N,N-dimethyl-formamide at -10℃; Inert atmosphere To a stirredsuspension of 3,5-dihydroxybenzaldehyde, 12 (2.76 g,20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF(50 mL) was added methyl iodide (1.25 mL, 20.0 mmol)dropwise at −10 C under nitrogen atmosphere. The mixturewas stirred for 3 h at this temperature. After completion of thereaction, water (70 mL) was added. The mixture was thenextracted with ether (2 × 80 mL), the combined organic layerwas washed with brine (2 × 80 mL), dried over anhydrousNa2SO4, filtered and the filtrate was concentrated in vacuo.The crude residue was purified by column chromatography(EtOAc/hexane = 1/4) to yield the compound 17 (1.19 g,39percent) as white solid. Rf = 0.23 (EtOAc/hexane = 1/4); mp128–130 C; 1H NMR (300 MHz, CDCl3) δ 9.86 (1H, s),6.98 (1H, dd, J = 2.4, 1.5 Hz), 6.95 (1H, dd, J = 2.4,1.5 Hz), 6.67 (1H, t, J = 2.4 Hz), 5.79 (1H, s), 3.84 (3H, s);13C NMR (75 MHz, CDCl3) δ 191.8, 161.3, 157.2, 138.4,109.0, 108.1, 107.0, 55.7.
39% With potassium carbonate In N,N-dimethyl-formamide at -10℃; for 3 h; Inert atmosphere To a suspension of 3,5-dihydroxybenzaldehyde (3,5-dihydroxybenzaldehyde, compound 12) (2.76 g, 20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF (50 mL) was added methyl iodide (1.25 mL, 20.0 mmol) in a nitrogen atmosphere, - 10°C. The reaction mixture was stirred at this temperature for three hours. After the reaction was completed, 70 ml of water was added. The reaction mixture was then extracted with ether (2 x 80 mL) and the combined organic layers were washed with brine (2 x 80 mL), dried over anhydrous Na2SO4,The filtrate was concentrated in vacuo. The crude compound was purified by column chromatography (EtOAc / hexane = 1/4) to obtain a white solid compound 17 (1.19 g, 39percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: at 20℃; for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at O0C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) was treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction was treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It was then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase was washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound was obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent)..
29%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h;
Stage #2: for 16 h;
Synthesis of Compound 394; 3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).

Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2907 - 2914
[2] Patent: KR2016/115127, 2016, A, . Location in patent: Paragraph 0018; 0019
[3] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 359-360
[4] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 256
[5] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 359-360
[6] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 359-360
  • 3
  • [ 67-56-1 ]
  • [ 26153-38-8 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
25% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 0.5 h; a)
3 Hydroxy-5-methoxybenzaldehyde
Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0 °C.
The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid.
The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane / petroleum ether (2: 1 then 100: 0)) to give the title compound (309 mg, 25percent) as a gum. 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98 - 6.99 (m, 2 H), 6.94 - 6.96 (m, 1 H), 3.80 (s, 3 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 1, p. 1 - 4
[2] Patent: EP906091, 2006, B1, . Location in patent: Page/Page column 21
  • 4
  • [ 7311-34-4 ]
  • [ 811-51-8 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: at 145℃; for 1.5 h;
Stage #2: at 145℃; for 1.13333 h;
Example 123
Preparation of 5,7-Dimethoxy-2-(3-methoxy-5-(2-(pyrrolidin-1-yl)ethoxy)phenyl)quinazolin-4(3H)-one
To a 1.0-L three-neck flask was added sodium ethanethiolate (80percent, 28.5 g, 271.0 mmol) and anhydrous DMF (225 mL).
The mixture was heated to 145° C. for 1.5 hours.
Then, 3,5-dimethoxy-benzaldehyde (15.0 g, 90.0 mmol) in anhydrous DMF (350 mL) was added over a period of 8 minutes.
The reaction was kept at 145° C. for another 1 hour, then cooled to room temperature.
Saturated sodium chloride solution (2.5 L) and formaline (37percent, 240 mL) together with acetic acid (500 mL) was added.
The resulting solution was thoroughly extracted with ethyl acetate, the organic phase was dried with sodium sulfate, and the solvent was removed under vacuum.
The crude compound was purified by column chromatography (silica gel 230-400 mesh; eluting with dichloromethane and ethyl acetate 7:1) to give 3-hydroxy-5-methoxy-benzaldehyde as a white solid. Yield: 12.0 g (88percent).
Reference: [1] Patent: US9238640, 2016, B2, . Location in patent: Page/Page column 151; 152; 153
  • 5
  • [ 908609-54-1 ]
  • [ 57179-35-8 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 2, p. 390 - 393
  • 6
  • [ 26153-38-8 ]
  • [ 1972-28-7 ]
  • [ 57179-35-8 ]
YieldReaction ConditionsOperation in experiment
25% With triphenylphosphine In tetrahydrofuran; methanol; Petroleum ether a
3-Hydroxy-5-methoxybenzaldehyde
Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0° C.
The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid.
The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane/petroleum ether (2:1 then 100:0)) to give the title compound (309 mg, 25percent) as a gum. 1 H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98-6.99 (m, 2 H), 6.94-6.96 (m, 1 H), 3.80 (s, 3 H).
Reference: [1] Patent: US5891909, 1999, A,
  • 7
  • [ 894077-48-6 ]
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Reference: [1] Patent: WO2006/63805, 2006, A1, . Location in patent: Page/Page column 72-73
  • 8
  • [ 97242-33-6 ]
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Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1424,1428
  • 9
  • [ 860590-75-6 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. &lt;2&gt; 116, p. 323
  • 10
  • [ 705-76-0 ]
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Reference: [1] Patent: WO2016/14529, 2016, A1,
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  • [ 19520-75-3 ]
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Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1424,1428
[2] Journal fuer Praktische Chemie (Leipzig), 1927, vol. &lt;2&gt; 116, p. 323
  • 12
  • [ 97242-30-3 ]
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Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1424,1428
  • 13
  • [ 860562-81-8 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. &lt;2&gt; 116, p. 323
  • 14
  • [ 2150-44-9 ]
  • [ 74-88-4 ]
  • [ 57179-35-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 49, p. 15746 - 15750[2] Angew. Chem., 2017, vol. 129, p. 15952 - 15957,6
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