Alternatived Products of [ 26455-31-2 ]
Alternatived Products of [ 26455-31-2 ]
Product Details of [ 26455-31-2 ]
| CAS No. : | 26455-31-2 |
MDL No. : | MFCD01327671 |
| Formula : |
C9H11NO3
|
Boiling Point : |
285.828°C at 760 mmHg |
| Linear Structure Formula : | - |
InChI Key : | N/A |
| M.W : | 181.19 g/mol |
Pubchem ID : | - |
| Synonyms : |
|
Application In Synthesis of [ 26455-31-2 ]
- Upstream synthesis route of [ 26455-31-2 ]
- Downstream synthetic route of [ 26455-31-2 ]
- 1
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[ 2741-16-4 ]
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[ 26455-31-2 ]
- 2
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[ 2741-16-4 ]
-
[ 26455-31-2 ]
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1-(4-Isopropoxy-phenylazo)-[2]naphthol
[ No CAS ]
- 3
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[ 26455-31-2 ]
-
[ 60515-72-2 ]
- 4
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[ 26455-31-2 ]
-
[ 7664-66-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With tin(ll) chloride; In ethanol; for 18h;Reflux; |
To a solution of the intermediate compound 4 (1 .76 mmol, 320 mg) in absolute EtOH (8 ml_), stannous chloride dehydrate (7.92 mmol, 1 .78 g) was added and the reaction mixture was heated to reflux for 18 h. Reaction mixture was diluted with aqueous 1 N NaOH solution and ethyl acetate. The aqueous layer was extracted with EtAcO. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuum to give intermediate 5 (239 mg, 90%) with no further purification. LC-MS: tR =1 .12 [M+H]+= 152 (method 3) |
- 5
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[ 350-46-9 ]
-
[ 67-63-0 ]
-
[ 26455-31-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 89% |
Stage #1: isopropyl alcohol With N-benzyl-trimethylammonium hydroxide for 0.166667h; Neat (no solvent);
Stage #2: 4-Fluoronitrobenzene at 70℃; for 0.75h; Neat (no solvent); |
|
| 84% |
With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃; |
|
| 76% |
With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol |
|
Reference：
[1]Location in patent: experimental part
Meshram; Goud, P. Ramesh; Reddy, B. Chennakesava; Kumar, D. Aravind
[Synthetic Communications, 2010, vol. 40, # 14, p. 2122 - 2129]
[2]Bunce, Richard A.; Easton, Kerry M.
[Organic Preparations and Procedures International, 2004, vol. 36, # 1, p. 76 - 81]
[3]Ramlall, Pratima; McClelland, Robert A.
[Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 2, p. 225 - 232]
[4]Rarick; Brewster; Dains
[Journal of the American Chemical Society, 1933, vol. 55, p. 1289]
- 6
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[ 100-02-7 ]
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[ 75-26-3 ]
-
[ 26455-31-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 99% |
With potassium carbonate In N,N-dimethyl-formamide at 105 - 120℃; for 1h; |
1-isopropoxy-4-nitrobenzene (5).
4-nitrophenol (10 g, 0.0719 mol) was dissolved in 25 mL ofanhydrous dimethylformamide (DMF). To that potassium carbonate (1.5 equivalents, 14.9 g, 0.10785 mol) and 2-bromopropane (1.5 equivalents, 10.12 mL, 0.10785 mol) were then added tothe flask while stirring. The suspension was then allowed to reflux at 120 °C for 1 h. The reaction was monitored via TLC (4:1 Hex:EA) and upon completion the reaction mixture wasvacuum filtered and the DMF was evaporated under reduced pressure. The reaction mixture was then dissolved in ethyl acetate and washed once with brine, once with 1 N sodium hydroxide, and then three times with brine. The organic layer was then dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. In all, 12.89 g of a yellow oil, 1-isopropoxy-4-nitrobenzene, was received with final yield of 99.0 %. |
|
With potassium carbonate; acetone |
|
|
With potassium carbonate In dimethyl sulfoxide at 70℃; |
2.2.2. synthesis of the 1-alkoxy-4-nitrobenzene (5-9)
General procedure: A DMSO solution (20 mL) of the corresponding bromo alkyl compounds(1.1 eq.) was added to a solution (20 mL) containing p-nitrophenolate(1 eq.) and potassium carbonate (1 eq.). The reaction mixture was stirred at 70 °C for 4 to 6 h. Upon cooling and addition of water (50 mL), the aqueous solution was extracted three times with dichloromethane.The desired products were recovered after evaporationof the organic layer. For 5, white crystalline material was obtained after recrystallization in DMSO/water (65%). For 6-9, the desired compound was recovered as a clear oil (60-85%) after purification by flash column chromatography using silica and petroleum/ether (8:2) as eluent. |
|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 5h; |
|
Reference：
[1]Arnatt, Christopher K.; Adams, Joanna L.; Zhang, Zhu; Haney, Kendra M.; Li, Guo; Zhang, Yan
[Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2319 - 2323]
[2]Allen; Gates
[Organic Syntheses, 1955, vol. Coll. Vol. III, p. 140]
[3]Lam, Quan; Cortez, Alejandro; Nguyen, Thanh Truc; Kato, Mallory; Cheruzel, Lionel
[Journal of Inorganic Biochemistry, 2016, vol. 158, p. 86 - 91]
[4]Yu, Ming-cheng; Yang, Feng; Ding, Xiao-yu; Sun, Nan-nan; Jiang, Zheng-yuan; Huang, Ya-fei; Yan, Yu-rong; Zhu, Chen; Xie, Qiong; Chen, Zhi-feng; Guo, Si-qi; Jiang, Hua-liang; Chen, Kai-xian; Luo, Cheng; Luo, Xiao-min; Chen, Shi-jie; Wang, Yong-hui
[Acta Pharmacologica Sinica, 2021, vol. 42, # 9, p. 1524 - 1534]
- 7
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[ 67-56-1 ]
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[ 100-00-5 ]
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[ 100-17-4 ]
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[ 26455-31-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 13 % Chromat.
2: 82 % Chromat. |
With potassium hydroxide In isopropyl alcohol at 75℃; for 7.7h; |
|
- 8
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[ 26455-31-2 ]
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4-isopropoxybenzenamine hydrochloride
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 97.8% |
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol for 16h; |
4-isopropoxybenzenamine hydrochloride salt (6).
Concentrated hydrochloric acid (1.3equivalents, 2.58 mL, 0.0313 mol) was added to 60 mL MeOH. To that 1-isopropoxy-4-nitrobenzene (5) (4.349 g, 0.02403) was added to the solution along with 10 % w/w palladium on carbon (0.435 g, 10 %). The flask was placed on a hydrogenator at 60 psi H2 gas for 16 h, andmonitored via TLC (20:1:0.01 DCM:MeOH:NH4OH). Once completed, the reaction mixture was vacuum filtered through celite, treated with activated carbon, filtered through celite, and then evaporated under reduced pressure. The obtained product was recrystallized with methanola nd diethyl ether and dried. In all, 4.402 g of a purple solid, 4-isopropoxybenzenamine hydrochloride salt, was received with a final yield of 97.8 %. |
|
With hydrogenchloride; hydrogen 1.) MeOH, 2.) Et2O; Yield given; Multistep reaction; |
|
Reference：
[1]Arnatt, Christopher K.; Adams, Joanna L.; Zhang, Zhu; Haney, Kendra M.; Li, Guo; Zhang, Yan
[Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2319 - 2323]
[2]Ramlall, Pratima; McClelland, Robert A.
[Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 2, p. 225 - 232]
- 9
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[ 26455-31-2 ]
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Fuller's earth
[ No CAS ]
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[ 60515-72-2 ]
- 10
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[ 100-02-7 ]
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[ 67-63-0 ]
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[ 26455-31-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 4-nitro-phenol; isopropyl alcohol With di-tert-butyl-diazodicarboxylate; resin bound PPh3 In dichloromethane at 0℃;
Stage #2: With trifluoroacetic acid In dichloromethane for 1h; |
|
|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16h; |
|
- 11
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[ 26455-31-2 ]
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cis-4-isopropoxy-cyclohexylamine
[ No CAS ]
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trans-4-isopropoxycyclohexylamine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With hydrogen; acetic acid In ethanol at 60℃; for 4h; |
113.113A
EXAMPLE 113; Preparation of trans-4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid (4-isopropoxy-cvclohexyl)-amide113 A. Preparation of 4-isopropoxy-cyclohexylamineA mixture of l-isopropoxy-4-nitrobenzene (500 mg, 2.76 mmol) and 5%Rh/alumina (400 mg) in EtOH (10 ml) and glacial AcOH (200 μl) was shaken under 50 psi of hydrogen at 60 °C for 4 hours. The mixture was filtered through a EPO plug of Celite and reduced in vacuo to give the title compound as a mixture of isomers. |
- 12
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[ 26455-31-2 ]
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[ 5210-99-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 76% |
With N-chloro-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 18h; |
1
To a solution of 1 -isopropoxy-4-nitrobenzene 1.1 (2 g, 1 1.0 mmol) in DMF(15 mL) was added ./V-chlorosuccinimide (NCS) ( 1.8 g, 13.2 mmol) at 0 0C. After stirring at 0 "C for 4 h, the reaction mixture was allowed to warm to room temperature and stirred for 14 h. The mixture was purified on RP-HPLC using a mixture of acetonitrile and HhO to give 1.2 ( 1.8 g, 76%), which was characterized by 1H NMR. |
- 13
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[ 67-63-0 ]
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[ 586-78-7 ]
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[ 26455-31-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 85% |
With bis(μ-iodo)bis[(-)-sparteine]-dicopper(I); caesium carbonate at 120℃; for 12h; |
|
- 14
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[ 3289-28-9 ]
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[ 26455-31-2 ]
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C16H23NO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
Stage #1: ethyl cyclohexanecarboxylate; 1-isopropoxy-4-nitrobenzene With chromium chloride; chloro-trimethyl-silane; magnesium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 90℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran |
|
- 15
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[ 93-89-0 ]
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[ 26455-31-2 ]
-
C16H17NO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 72% |
Stage #1: benzoic acid ethyl ester; 1-isopropoxy-4-nitrobenzene With chromium chloride; chloro-trimethyl-silane; magnesium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 90℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran |
|
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