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[ CAS No. 7153-22-2 ] {[proInfo.proName]}

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Chemical Structure| 7153-22-2
Chemical Structure| 7153-22-2
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Product Details of [ 7153-22-2 ]

CAS No. :7153-22-2 MDL No. :MFCD00001824
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JLSSWDFCYXSLQX-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :81589
Synonyms :

Calculated chemistry of [ 7153-22-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.24
TPSA : 50.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.562 mg/ml ; 0.00321 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.197 mg/ml ; 0.00113 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.192 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 7153-22-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7153-22-2 ]

* 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 [ 7153-22-2 ]
  • Downstream synthetic route of [ 7153-22-2 ]

[ 7153-22-2 ] Synthesis Path-Upstream   1~67

  • 1
  • [ 64-17-5 ]
  • [ 105-07-7 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
85% at 50 - 60℃; Ionic liquid General procedure: Arylaldehyde (25 mmol) and [bmim]N3 (75 mmol) and alcohol (75 mmol) were mixed thoroughly and stirred at 50–60 C. The completion of reaction was monitored by TLC using (EtOAc/petroleum ether 1:7) as eluent and the product was isolated via preparative chromatography from EtOAc/petroleum ether as eluent.
26 %Spectr. With C39H80N6Si6Th In benzene-d6 at 70℃; for 24 h; Sealed tube General procedure: In a typical experiment, a J. Young Teflon sealed NMR tube was charged with the desired amount of the catalyst from a stock solution of C6D6. Aldehyde (150 equiv) and alcohol (50 equiv) (TFMAP was added if necessary) were added and the reaction mixture was diluted with C6D6. Samples were then sealed and placed in an oil bath preheated to 70°C. The progress of reaction was monitored at regular intervals using 1H NMR spectroscopy for up to 24h. The yield was calculated from the ratio of esters and alcohols from the crude 1H NMR spectra. The 1H NMR spectra of ester products, including methyl benzoate, ethyl benzoate, isopropyl benzoate, methyl 4-nitrobenzoate, methyl 4-cyanobenzoate, methyl 3-nitrobenzoate, methyl 4-methylbenzoate, methyl 2-furoate, methyl naphthalene-1-carboxylate, were compared with previous reports [60].
Reference: [1] Synthesis, 2010, # 2, p. 276 - 282
[2] Comptes Rendus Chimie, 2012, vol. 15, # 11-12, p. 1077 - 1080
[3] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2070 - 2072
[4] Journal of Organometallic Chemistry, 2018, vol. 857, p. 123 - 137
  • 2
  • [ 64-17-5 ]
  • [ 619-65-8 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
84% for 12 h; Reflux To a stirred solution of 4-cyanobenzoic acid (XXII; 10 g; 68 mmol) in ethanol (150 mL) was added a catalytic quantity of sulfuric acid (1 mL). The reaction mixture was heated to a reflux for 12 hours. The reaction mixture was cooled, concentrated at reduced pressure and dilutedwith water. The aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed sequentially with sodium bicarbonate and brine, then dried over Na2SO4, filtered and concentrated under vacuum to afford ethyl 4-cyanobenzoate as a white solid (XXIII; 10 g, 84percent yield). ‘H NMR (400 MHz, DMSO-d6) ö 8.10-8.08 (d, J = 8.4 Hz, 2H), 8.01-7.99 (d, J = 8.4 Hz, 2H), 4.37-4.32 (q, J = 7.2 Hz, 2H), 1.35-1.3 1 (t, J = 7.2 Hz,3H).
73% at 20℃; Reflux Example 22; 2-chloro-4-((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropylamino)-3-methylbenzonitrile; Intermediate 22a; Ethyl 4-cyanobenzoate; To a 250 mL round bottom flask charged with 4-cyanobenzoic acid (19.36 g, 0.13 mol) in abs. ethanol (100 mL) was added concentrated sulfuric acid (3 mL). This mixture was heated to reflux for a period of 28 h, then allowed to cool to room temperature overnight. The solvent was removed via rotary evaporation and the resulting off-white residue was taken up in diethyl ether (500 mL). This was then washed with saturated sodium bicarbonate/water solution (5.x.100 mL), then brine (1.x.100 mL), and dried over magnesium sulfate. Filtration and concentration yielded an off-white solid. Recrystallization from 95percent ethanol (50 mL) yielded product as white crystals (16.85 g, 73percent). 1H NMR (400 MHz, CDCl3, δ in ppm) 8.14 (AA'XX', J=8.6 Hz, 2H), 7.74 (AA'XX', J=8.6 Hz, 2H), 4.42 (q, J=7.1 Hz, 2H), 1.41 (t, J=7.1 Hz, 3H).
71% at 100℃; for 24 h; General procedure: A mixture of acid (0.2 mmol), alcohol (0.6 mmol) and GO (50 wtpercent, calculated with the mass of acid) in ethyl alcohol or DCE (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred at 100 °C for 24 h. After the reaction was finished, filtered the GO, solvent was removed, and the residue was separated by column chromatography to give the pure sample.
Reference: [1] Patent: WO2015/97122, 2015, A1, . Location in patent: Page/Page column 86
[2] Patent: US2009/253758, 2009, A1, . Location in patent: Page/Page column 54
[3] Synlett, 2017, vol. 28, # 8, p. 981 - 985
[4] Chemical Communications, 2016, vol. 52, # 55, p. 8569 - 8572
[5] Asian Journal of Chemistry, 2016, vol. 28, # 3, p. 639 - 643
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 207 - 212
  • 3
  • [ 51934-41-9 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -15℃; for 0.25 h;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2 h;
General procedure: To a flask containing dried LiCl (0.35 g, 8.24 mmol) was added iPrMgCl (2 M in THF, 4.1 mL) and THF (5 mL) at 15° C. After beingstirred for 15 min, 3-bromo-1-benzonitrile (1.46 g, 8.03 mmol) inTHF (1 mL) was added to the reaction mixture and the obtainedmixture was stirred for 15 min. Then, DMF (1.3 mL, 12 mmol) wasadded at 0° C and the mixture was stirred for 2 h. Then, aq NH3 (7 mL, 28-30percent) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After being stirred for 2 h at room temperature, the reactionmixture was poured into satd aq Na2SO3 solution and was extracted with CHCl3 (3∗30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure 1,3-dicyanobenzene (0.73 g) in 71percent yield. Most nitriles mentioned in this work are commercially availableand were identified by comparison with the authentic samples.
Reference: [1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469
  • 4
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  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
84% With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 3 h; Inert atmosphere; Sealed tube General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1,11.9mg), dppf (0.06mmol, 33.3mg), Zn (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Zn(CN)2 (0.8mmol) , 93.9mg), p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 °C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88percent, and 1H NMR purity was greater than 98percent.
Reference: [1] Organic Letters, 2017, vol. 19, # 8, p. 2118 - 2121
[2] Patent: CN108623495, 2018, A, . Location in patent: Paragraph 0043; 0045; 0169-0171
  • 5
  • [ 1204518-04-6 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
87% With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 2 h; General procedure: A mixture of diaryliodonium salt (0.5 mmol), K4[Fe(CN)6] (184.2 mg, 0.5 mmol), Pd(OAc)2 (5.6 mg, 0.025 mmol), K2CO3 (138.2 mg, 1 mmol), and DMF (1 mL) was taken in a 10 ml reaction tube and heated at 130 °C for 2 h under vigorous stirring. After completion of the reaction (observed on TLC or GC), the mass was cooled to room temperature, and 5 ml of water was added. The mixture was stirred for 10 min and extracted with ethyl acetate (3 × 10 mL). The organic layer was washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure and the residue was purified on silica gel column by using petroleum ether and ethyl acetate as eluent to obtain the pure product. All the compounds were analyzed by 1H NMR, 13C NMR, and mass spectra.#10;
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 51, p. 6954 - 6956
  • 6
  • [ 64-17-5 ]
  • [ 874-89-5 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
89% With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 17 h; Green chemistry General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 °C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82percent).
Reference: [1] Synlett, 2018, vol. 29, # 16, p. 2208 - 2212
  • 7
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  • [ 57-13-6 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
84% With copper (II)-fluoride; 1,10-Phenanthroline; oxygen; lithium carbonate In dimethyl sulfoxide at 150℃; for 36 h; Sealed tube General procedure: Under Oxygen, a reaction tube was charged with p-iodoanisole (46.3 mg, 0.2 mmol), urea (48.0 mg, 0.8 mmol), CuF2 (4.1 mg, 0.04 mmol), L1 (10.8 mg, 0.06 mmol), Li2CO3 (44.3 mg, 0.6mmol) and DMSO (2 mL). The mixture was stirred at 150 oC for 36 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5250 - 5252
  • 8
  • [ 383-63-1 ]
  • [ 30611-20-2 ]
  • [ 7153-22-2 ]
  • [ 360-34-9 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.166667 h; Inert atmosphere; Schlenk technique
Stage #2: at 0℃; for 5 h; Inert atmosphere; Schlenk technique; Reflux
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25 h; Inert atmosphere; Schlenk technique
General procedure: Under Ar atmosphere in a dry Schlenk tube, a mixture of NaH (6.0 mmol) and trifluoroacetate (6.0 mmol) was stirred in THF (5 mL) at room temperature for 10 min. To this mixture enolizable ketones (5.0 mmol) in THF (5 mL) was added dropwise at 0 °C under Ar atmosphere. After stirring for 2–6 h at reaction temperature, the reaction solution was cooled to 0 °C again and quenched with 6 mL of 1 mol/L HCl. After stirring for additional 15 min, the mixture was neutralized with saturated NaHCO3 solution. After usual workup, the residue was purified by chromatography on silica gel to afford the trifluoromethyl alkyl ketone products.#10;
Reference: [1] Tetrahedron, 2014, vol. 70, # 31, p. 4668 - 4674
  • 9
  • [ 623-00-7 ]
  • [ 1906-57-6 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
74% With palladium diacetate In 1-methyl-pyrrolidin-2-one at 20 - 140℃; for 24 h; Inert atmosphere General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol percent), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 43, p. 5796 - 5799
  • 10
  • [ 623-00-7 ]
  • [ 109-94-4 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 15 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 11
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  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
49% With palladium dichloride; silver(l) oxide In ethanol at 70℃; for 24 h; General procedure: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1205 - 1209
[2] Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3419 - 3423
  • 12
  • [ 64-17-5 ]
  • [ 3058-39-7 ]
  • [ 13939-06-5 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
69% With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N-ethyl-N,N-diisopropylamine In neat (no solvent) at 130℃; for 0.25 h; Microwave irradiation General procedure: A mixture of the aryl halide (1.0 mmol), alcohol (5.0 equiv), Mo(CO)6 (0.5 equiv), DIPEA (1.5 equiv) and palladacycle 1 (1 mol percent Pd) was heated in a pressure tube at 130 °C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixture was cooled to room temperature and the alcohol was removed. The crude mixture was subjected to F-SPE to remove palladacycle 1 (see general procedure for the recycling of palladacycle 1) and the solution of crude product was concentrated, diluted with EtOAc (20 mL) and washed successively with 2 M HCl (210 mL) and water (10 mL). The organic layer was driedover anhydrous MgSO4, filtered and concentrated to give pure 6.
Reference: [1] Tetrahedron, 2014, vol. 70, # 45, p. 8545 - 8558
  • 13
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  • [ 21864-90-4 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
58% With palladium diacetate; copper(II) trifluoroacetate In N,N-dimethyl-formamide at 120℃; for 24 h; Sealed tube General procedure: Aryl halide (0.5 mmol), α-Iminonitrile (0.6 mmol), Cu(TFA)2 (1.0 mmol), Pd(OAc)2(0.1 mmol) and 2ml DMF were added into a 15 ml sealed tube with a magneticstirring bar. Stirred under air at 120°C for 24 h. Monitor the reaction by TLC. Themixture was poured into water (10 ml) and extracted by ethyl acetate (3×10 ml).Dried by Na2SO4 and evaporated. Finally, pure the mixture by silica gel column.
Reference: [1] Synlett, 2018, vol. 29, # 3, p. 359 - 363
  • 14
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Reference: [1] Organic Letters, 2004, vol. 6, # 17, p. 2837 - 2840
  • 15
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YieldReaction ConditionsOperation in experiment
36% With palladium dichloride; silver(l) oxide In ethanol at 70℃; for 24 h; General procedure: a.Cyanation of aryl iodides.To a solution of aryl iodide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 h under air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2, petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1205 - 1209
  • 16
  • [ 5798-75-4 ]
  • [ 557-21-1 ]
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 7, p. 1441 - 1444
  • 17
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Reference: [1] Synlett, 2007, # 4, p. 543 - 546
  • 18
  • [ 623-26-7 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
33% With sulfuric acid In ethanol; water Example 37
Terephthalonitrile (12.8 g), 95percent sulfuric acid (10.3 g), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130° C. for six hours.
The reaction mixture was cooled, and water (9 g) was added thereto.
Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 33percent and a selectivity of 83percent.
30% With hydrogenchloride In ethanol; water Example 38
Terephthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130° C. for six hours.
The reaction mixture was cooled, and water (9 g) was added thereto.
Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 30percent and a selectivity of 96percent.
Reference: [1] Patent: US6433211, 2002, B1,
[2] Patent: US6433211, 2002, B1,
  • 19
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  • [ 7153-22-2 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
  • 20
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Reference: [1] Organic Letters, 2018, vol. 20, # 17, p. 5098 - 5102
  • 21
  • [ 5798-75-4 ]
  • [ 201230-82-2 ]
  • [ 68-12-2 ]
  • [ 7153-22-2 ]
  • [ 67052-28-2 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 43, p. 10722 - 10723
  • 22
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  • [ 94-09-7 ]
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Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1205 - 1209
  • 23
  • [ 124-38-9 ]
  • [ 51934-41-9 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
78 %Chromat. With phenylsilane; ammonia; copper(II) acetylacetonate In N,N-dimethyl-formamide at 160℃; for 10 h; Sealed tube Under a nitrogen atmosphere, copper acetylacetonate (20 molpercent, 6.6 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Subsequently, N,N-dimethylformamide (0.5 mL), ethyl 4-iodobenzoate (0.125 mmol, 1.0 equiv., 34.5 mg) and phenylsilane (3.0 equiv., 40.6 mg) were added. The pressure tube was sealed, the tube air was removed and charged with carbon dioxide (0.67 mmol, 5.0 equiv., 15 mL) and ammonia gas (0.67 mmol, 5.0 equiv., 15 mL). After the addition, the glass pressure tube was placed in a metal module that had been preheated to 160°C and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Using dodecane as an internal standard, the yield of the gas chromatography was determined to be 78percent.
Reference: [1] Patent: CN108017557, 2018, A, . Location in patent: Paragraph 0062-0064
  • 24
  • [ 64-17-5 ]
  • [ 106456-85-3 ]
  • [ 7153-22-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 3, p. 506 - 508
  • 25
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Reference: [1] RSC Advances, 2013, vol. 3, # 43, p. 20379 - 20384
  • 26
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  • [ 201230-82-2 ]
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Reference: [1] Tetrahedron, 2008, vol. 64, # 40, p. 9581 - 9584
  • 27
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Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4115 - 4122
  • 28
  • [ 10602-03-6 ]
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Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3056 - 3059
  • 29
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 28, p. 10999 - 11005
  • 30
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Reference: [1] New Journal of Chemistry, 2012, vol. 36, # 11, p. 2334 - 2339
  • 31
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Reference: [1] Chinese Journal of Chemistry, 2013, vol. 31, # 4, p. 449 - 452
  • 32
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 10035 - 10039[2] Angew. Chem., 2013, vol. 125, # 38, p. 10219 - 10223
  • 33
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Reference: [1] Chemical Science, 2017, vol. 8, # 12, p. 8094 - 8105
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  • [ 7153-22-2 ]
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YieldReaction ConditionsOperation in experiment
90% With hydrazine hydrate In ethanol; water at 20℃; for 20.5 h; Reflux Intermediate 22b; 4-Cyanobenzohydrazide; To a 250 mL round bottom flask charged with ethyl 4-cyanobenzoate (16.85 g, 96.2 mmol) in 95percent ethanol (75 mL) was added hydrazine mono-hydrate (18.2 mL, 64percent solution, 240 mmol). This mixture was heated to reflux for a period of 4.5 h, then allowed to cool to room temperature over a 16 h period. The solvent was removed under reduced pressure and the yellow residue was taken up in ice-cold water (150 mL). The light yellow solid was filtered off and washed with additional cold water (50 mL). The solid was then dried under high vacuum to yield the title compound as a light yellow solid (13.98 g, 90percent). 1H NMR (400 MHz, DMSO-d6, δ in ppm) 10.05 (br s, 1H), 7.95 (AA'XX', J=8.5 Hz, 4H), 4.61 (br s, 2H).
Reference: [1] Patent: US2009/253758, 2009, A1, . Location in patent: Page/Page column 55
[2] An. Esc. super. Quim. Univ. Recife, 1959, vol. 1, p. 41 - 53
[3] Asian Journal of Chemistry, 2016, vol. 28, # 3, p. 639 - 643
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 207 - 212
  • 63
  • [ 7153-22-2 ]
  • [ 64-17-5 ]
  • [ 874-89-5 ]
YieldReaction ConditionsOperation in experiment
60 %Spectr. With C21H35BrMnN2O2P; hydrogen; potassium hydride In toluene at 100℃; for 60 h; Hydrogenation of 1 mmol of hexyl hexanoate under 20 bar at 100°C in toluene, resulted in 99percent yield of hexanol (Entry 1). Under the same conditions ethyl butyrate was hydrogenated to give 98percent yield of butanol and 91 percent yield of ethanol after 50 hours (Entry 2). When the reaction was performed at shorter reaction time (22 hours, Entry 2bis), small amounts of ethyl acetate and butyl butanoate were also formed, attributed to a transesterification reaction with the formed ethanol and butanol. Cyclohexylmethyl acetate gave 99percent yield of cyclohexylmethanol and 60percent yield of ethanol (Entry 3), and no transesterification products were observed. Hydrogenation of the secondary aliphatic ester heptan-2-yl acetate resulted in 98percent yield of heptane-2-ol and 57percent yield of ethanol (Entry 4). Ethyl 3-phenylpropanoate was smoothly hydrogenated, rendering 99percent yield of 3-phenylpropan-l-ol and 70percent yield of ethanol after 21 hours (Entry 5). Similarly, ethyl 3- phenylpropanoate gave 99percent yield of phenyknethanol and 74percent yield of butanol after 22 hours (Entry 6). In order to get full hydrogenation of benzyl benzoate longer reaction time was needed (43 hours, 99percent yield benzyl alcohol, Entry 7). Similarly, methyl benzoate gave 96percent yield of benzyl alcohol and 63 percent of methanol after 50 hours (Entry 8). ε-Caprolactone was smoothly and quantitatively hydrogenated to 1 ,6-hexanediol (99percent yield, Entry 9). The activated benzyl trifluoroacetate gave 99percent yield of benzyl alcohol and 78percent of 2,2,2- trifluoroethanol (Entry 10), and no secondary products where observed. Gratifyingly, allyl trifluoroacetate gave 97percent yield of 2,2,2-trifluoroethanol and 96percent of allyl alcohol (Entry 1 1), showing high chemoselectivity to ester hydrogenation over C=C hydrogenation. Hydrogenation of ethyl 4-isocyano-benzoate required an increase of precatalyst loading to 3percent, probably due to competing nitrile coordination, and resulted in 61 percent yield of (4-isocyanophenyl)methanol and 66percent yield of ethanol, with no hydrogenation of the nitrile group detected (Entry 12).
Reference: [1] Patent: WO2017/137984, 2017, A1, . Location in patent: Paragraph 00352-00353
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Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 4, p. 529 - 532
[2] Chemistry - A European Journal, 2011, vol. 17, # 27, p. 7414 - 7417
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Reference: [1] Justus Liebigs Annalen der Chemie, 1959, vol. 628, p. 172,181
  • 66
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Reference: [1] Inorganic Chemistry, 2018, vol. 57, # 24, p. 15069 - 15078
[2] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 257,258
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 2514
  • 67
  • [ 7153-22-2 ]
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  • [ 131065-88-8 ]
Reference: [1] Helvetica Chimica Acta, 1930, vol. 13, p. 457,470
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