Alternatived Products of [ 35674-28-3 ]
Product Details of [ 35674-28-3 ]
CAS No. : 35674-28-3
MDL No. : MFCD07783659
Formula :
C7 H4 INO4
Boiling Point : -
Linear Structure Formula : -
InChI Key : RYOSQAPCAPOLCV-UHFFFAOYSA-N
M.W :
293.02
Pubchem ID : 13756757
Synonyms :
Application In Synthesis of [ 35674-28-3 ]
* 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 [ 35674-28-3 ] Downstream synthetic route of [ 35674-28-3 ]
1
[ 35674-28-3 ] [ 5326-47-6 ]
Reference：
[1] Journal fuer Praktische Chemie (Leipzig), 1878, vol. <2> 18, p. 326
1
[ 35674-28-3 ]
[ 5326-47-6 ]
Yield Reaction Conditions Operation in experiment
With acetic acid
bei der Reduktion;
With palladium on activated charcoal; hydrogen
Reference：
[1]Grothe
[Journal fur praktische Chemie (Leipzig 1954), 1878, vol. <2> 18, p. 326]
[2]Grothe
[Journal fur praktische Chemie (Leipzig 1954), 1878, vol. <2> 18, p. 326]
[3]Dong, Kui-Kui; Zhou, Hua-Hong; Guo, A-Rong; Chen, Tian; Wang, Yu-Liang
[Asian Journal of Chemistry, 2013, vol. 25, # 2, p. 1039 - 1042]
2
[ 13280-60-9 ]
[ 35674-28-3 ]
Yield Reaction Conditions Operation in experiment
a) 5-Iodo-2-nitrobenzoic acid Sulfuric acid (40 mL) was poured into water (240 mL). After the solution was cooled down to 0 C., <strong>[13280-60-9]5-amino-2-nitrobenzoic acid</strong> (23.6 g) was added, and then phosphoric acid (200 mL) was further added thereto. After cooling down to 10 C., an aqueous solution (20 mL) of sodium nitrite (9.2 g) was added dropwise thereto over 15 minutes. The mixture was stirred at room temperature for 1 hour and filtered through a Celite pad. The filtrate was added dropwise to an aqueous solution (400 mL) of potassium iodide (30 g). After the mixture was stirred at room temperature overnight, the resulting precipitated solid was filtered to give the title compound (30.0 g).
3
[ 35674-28-3 ]
[ 150022-33-6 ]
Yield Reaction Conditions Operation in experiment
90%
With borane In tetrahydrofuran for 1h; Heating;
57%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 24h;
9.a
EXAMPLE 9a Preparation of intermediate 5-Iodo-2-nitro-benzaldehyde To a solution of 5-iodo-2-nitrobenzoic acid (37 g, 126 mmol) (APIN) in anhydrous tetrahydrofuran (200 mL) at 0° C. was added borane tetrahydrofuran (1 M, 360 mL, 360 mmol) dropwise. The reaction mixture was then stirred at room temperature for 24 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, concentrated, and triturated. The precipitate 5-Iodo-2-nitro-phenyl)-methanol was collected as a yellow solid (20 g, 57%). The solid (5.5 g) was dissolved into dichloromethane (100 mL), and activated MnO2 (15 g) was added. The mixture was then heated at reflux for 4 h, cooled to room temperature, and filtered through a short pad of celite. The filtrated was concentrated to give 5-Iodo-2-nitro-benzaldehyde as a yellow solid (Yield 4.2 g, 76%).
With dimethylsulfide borane complex In tetrahydrofuran for 2h; Heating;
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
[2]Current Patent Assignee: ROCHE HOLDING AG - US2009/156610, 2009, A1
Location in patent: Page/Page column 16
[3]Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J.
[Journal of Medicinal Chemistry, 1987, vol. 30, # 2, p. 303 - 318]
4
[ 7697-37-2 ]
[ 618-51-9 ]
[ 35674-28-3 ]
3-iodo-4-nitrobenzoic acid
[ No CAS ]
3-iodo-2-nitro-benzoic acid
[ No CAS ]
5
[ 618-51-9 ]
[ 35674-28-3 ]
Yield Reaction Conditions Operation in experiment
With nitric acid
6
[ 35674-28-3 ]
[ 53279-83-7 ]
Yield Reaction Conditions Operation in experiment
With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran
7
[ 35674-28-3 ]
[ 914777-94-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 78 percent / aqueous sodium carbonate / tetrakis(triphenylphosphine)palladium(0) / toluene; ethanol / 2.5 h / Heating
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
8
[ 35674-28-3 ]
[ 914777-96-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 34 percent / silver nitrate; triphenylphosphine; triethylamine / palladium acetate / acetonitrile / 120 h / Heating
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
9
[ 35674-28-3 ]
[ 914777-95-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 89 percent / piperidine / tetrakis(triphenylphosphine)palladium; copper(I) iodide / 2 h / 20 °C
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
10
[ 35674-28-3 ]
1-(4-nitrophenoxymethyl)-5-(4-methoxy-phenyl)-2-nitrobenzene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 78 percent / aqueous sodium carbonate / tetrakis(triphenylphosphine)palladium(0) / toluene; ethanol / 2.5 h / Heating
3: 31 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / Heating
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
11
[ 35674-28-3 ]
1-(4-nitrophenoxymethyl)-5-(4-methoxy-phenylethylene)-2-nitrobenzene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 34 percent / silver nitrate; triphenylphosphine; triethylamine / palladium acetate / acetonitrile / 120 h / Heating
3: 30 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / Heating
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
12
[ 35674-28-3 ]
1-(4-nitrophenoxymethyl)-5-(4-methoxy-phenylethynyl)-2-nitrobenzene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 89 percent / piperidine / tetrakis(triphenylphosphine)palladium; copper(I) iodide / 2 h / 20 °C
3: 75 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
13
[ 35674-28-3 ]
[ 914778-18-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 52 percent / 4-dimethylaminopyridine; dicyclohexycarbodiimide / CH2 Cl2 / 0 - 20 °C
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
14
[ 35674-28-3 ]
7-diethylamino-2-oxo-2H-chromene-3-carboxylic acid 5-(4-methoxy-phenylethylene)-2-nitrobenzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 52 percent / 4-dimethylaminopyridine; dicyclohexycarbodiimide / CH2 Cl2 / 0 - 20 °C
3: 43 percent / silver nitrate; triphenylphosphine; triethylamine / palladium acetate / acetonitrile / 144 h / Heating
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
15
[ 35674-28-3 ]
7-diethylamino-2-oxo-2H-chromene-3-carboxylic acid 5-(4-methoxy-phenylethynyl)-2-nitrobenzyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / borane / tetrahydrofuran / 1 h / Heating
2: 52 percent / 4-dimethylaminopyridine; dicyclohexycarbodiimide / CH2 Cl2 / 0 - 20 °C
3: 61 percent / piperidine; copper(I) iodide / tetrakis(triphenylphosphine)palladium; copper(I) iodide / 4 h / 20 °C
Reference：
[1]Aujard, Isabelle; Benbrahim, Chouaha; Gouget, Marine; Ruel, Odile; Baudin, Jean-Bernard; Neveu, Pierre; Jullien, Ludovic
[Chemistry - A European Journal, 2006, vol. 12, # 26, p. 6865 - 6879]
16
[ 35674-28-3 ]
6-iodo-1,4-dihydro-benzo[<i>d</i>][1,3]oxazin-2-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: NaBH4 ; ZnCl2 / tetrahydrofuran
2: NaH / tetrahydrofuran
17
[ 35674-28-3 ]
(2-oxo-1,4-dihydro-2H-benzo[1,3]oxazin-6-yl)phosphonic acid benzyl ester ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: NaBH4 ; ZnCl2 / tetrahydrofuran
2: NaH / tetrahydrofuran
3: Et3 N; Et3 SiH / PdCl2 dppf / toluene
18
[ 35674-28-3 ]
[ 105728-31-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
19
[ 35674-28-3 ]
[ 105728-32-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
20
[ 35674-28-3 ]
5-(2-Oxo-1,2,3,5-tetrahydro-imidazo[2,1-b]quinazolin-7-yl)-pentanoic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
4: 1.) AcONa / ethanol / 0.5 h
5: 1.) NaBH3 CN, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, 3 h, 2.) EtOH
6: 2.) conc. aq. NH3 / 1.) EtOH, RT, overnight, 2.) EtOH, RT, 30 min
7: Bu4 NBr, aq. KOH / dimethylformamide
21
[ 35674-28-3 ]
[ 105728-33-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
4: 1.) AcONa / ethanol / 0.5 h
5: 1.) NaBH3 CN, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, 3 h, 2.) EtOH
6: 2.) conc. aq. NH3 / 1.) EtOH, RT, overnight, 2.) EtOH, RT, 30 min
22
[ 35674-28-3 ]
5-{4-Amino-3-[(ethoxycarbonylmethyl-amino)-methyl]-phenyl}-pentanoic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
4: 1.) AcONa / ethanol / 0.5 h
5: 1.) NaBH3 CN, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, 3 h, 2.) EtOH
23
[ 35674-28-3 ]
5-{3-[(E)-Ethoxycarbonylmethylimino-methyl]-4-nitro-phenyl}-pent-4-ynoic acid methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
4: 1.) AcONa / ethanol / 0.5 h
24
[ 35674-28-3 ]
[ 105727-90-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: Me2 S*BH3 / tetrahydrofuran / 2 h / Heating
2: pyridinium dichromate / CH2 Cl2 / Heating
3: 77 percent / (Ph3 P)2PdCl2 , CuI, Et3 N / 0.5 h / 60 °C
4: 1.) AcONa / ethanol / 0.5 h
5: 1.) NaBH3 CN, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, 3 h, 2.) EtOH
6: 2.) conc. aq. NH3 / 1.) EtOH, RT, overnight, 2.) EtOH, RT, 30 min
7: Bu4 NBr, aq. KOH / dimethylformamide
8: bis(p-nitrophenyl) phenylphosphonate / dimethylformamide / 72 h
25
[ 99-05-8 ]
[ 35674-28-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: alcohol / man behandelt die Diazoaminobenzoesaeure mit Jod in Aether
2: concentrated nitric acid
Multi-step reaction with 2 steps
1: diluted sulfuric acid; concentrated potassium iodide / man leitet salpetrige Saeure ein
2: concentrated nitric acid
26
[ 35674-28-3 ]
[ 124-40-3 ]
[ 883241-41-6 ]
Yield Reaction Conditions Operation in experiment
Stage #1: 5-iodo-2-nitrobenzoic acid With oxalyl dichloride In chloroform at 20℃; for 2h;
Stage #2: dimethyl amine With sodium hydrogencarbonate In water; ethyl acetate; toluene at 0℃;
1.1.b 3-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid phenyl ester (Compound 1-1)
b) 5-Iodo-N,N-dimethyl-2-nitrobenzamide 5-Iodo-2-nitrobenzoic acid (15.5 g) was dissolved in chloroform (30 mL). Oxalyl chloride (13.4 g) was added thereto at 0° C., and then DMF (dimethylformamide) (0.1 mL) was further added. The mixture was stirred at room temperature for 2 hours, and then concentrated. After addition of toluene to the residue, the mixture was further concentrated. A solution of the concentrated residue in ethyl acetate (60 mL) was added dropwise to a mixed solution of 50% (w/w) aqueous dimethylamine (7.5 mL), saturated aqueous sodium bicarbonate (60 mL), and toluene (60 mL) under stirring and ice-cooling. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and saturated brine, and concentrated to give the title compound (15.3 g).
27
[ 52415-00-6 ]
[ 35674-28-3 ]
Yield Reaction Conditions Operation in experiment
With potassium permanganate; tetrabutylammomium bromide
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