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CAS No. : | 613-46-7 | MDL No. : | MFCD00016807 |
Formula : | C11H7N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AZKDTTQQTKDXLH-UHFFFAOYSA-N |
M.W : | 153.18 | Pubchem ID : | 11944 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.66 |
TPSA : | 23.79 Ų |
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) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 2.68 |
Log Po/w (WLOGP) : | 2.71 |
Log Po/w (MLOGP) : | 2.48 |
Log Po/w (SILICOS-IT) : | 2.98 |
Consensus Log Po/w : | 2.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.09 |
Solubility : | 0.123 mg/ml ; 0.000804 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.226 mg/ml ; 0.00147 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.14 |
Solubility : | 0.011 mg/ml ; 0.0000721 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.28 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 2-naphthalenecarbonitrile; ethylmagnesium bromide In diethyl ether at 20 - 25℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether at 0 - 20℃; | |
With diethyl ether anschliessendes Behandeln mit Eis und wss. HCl und Kochen der erhaltenen wss. Loesung; | ||
With toluene anschliessendes Behandeln mit Eis und wss. HCl und Kochen der erhaltenen wss. Loesung; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | General procedure: A flame-dried resealable 2-5 mL Pyrex reaction vessel was charged with the solid reactant(s): (hetero)aryl nitriles 1 (1.0 mmol) and Cs2CO3 (1.5 mmol). The reaction vessel was capped with a rubber septum, and pyrrolidinone (2 mL per mmol [0.5 M]) was added through the septum. The septum was replaced with a teflon screwcap. The reaction vessel was sealed and heated at 130 °C for 2 h. The resulting suspension was cooled to room temperature and filtered through a pad of celite eluting with CH2Cl2/MeOH (7:3), and the inorganic salts were removed. The filtrate was concentrated and purification of the residue by silica gel column chromatography gave the desired product. | |
88% | With water; at 110℃; for 6h; | General procedure: Two milli liter water at room temperature was added to astirred mixture of nitrile (1mmol) and catalyst (40mg) thenheated with an oil bath maintained at 110°C, and stirred. After completion of the reaction (monitored by TLC), thecatalyst was removed from the reaction mixture by externalmagnet. Then the mixture was extracted with ethyl acetate,subsequently purified by column chromatography on silicagel to provide the corresponding amide products. |
70%Chromat. | With [Ru(CO)(pyridoxal-4-methyl-thiosemicarbazide hydrochloride)(triphenylphosphine)2]; In methanol; water; at 80℃; for 1h;Catalytic behavior; | General procedure: Organic nitrile (1 mmol) and distilled water (1 mL) were sequentially added to 3 mL methanol solution of the ruthenium catalyst (0.3 molpercent) and the reaction mixture was stirred at 80°C. After completion of reaction, the catalyst was extracted from the reaction mixture by the addition of CH2Cl2/petroleum ether followed by filtration. The filtrate was subjected to GC analysis and the product was identified and determined with authentic samples |
With C40H45ClN3O2PRu; In methanol; water; at 20℃; for 4h;Inert atmosphere; Schlenk technique; Green chemistry;Catalytic behavior; | General procedure: Organic nitrile (1 mmol) and distilled water (1 mL) were sequentially added to 3 mL methanol solution of the [Ru?NHC] catalyst (0.5 molpercent) and the reaction mixture was stirred at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of reaction the catalyst was extracted from the reaction mixture by the addition of CH2Cl2/petroleum ether followed by filtration. The filtrate was subjected to GC analysis and the product was identified with authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With lithium aluminium tetrahydride In diethyl ether at 20℃; for 5h; Inert atmosphere; Cooling with ice; | |
86% | With potassium hydroxide; samarium diiodide In tetrahydrofuran for 0.0666667h; Ambient temperature; | |
84% | With boron trifluoride-tetrahydrofuran complex for 48h; Heating; |
82% | With methanol; sodium tetrahydroborate at 20℃; for 3h; | |
79% | With C28H29Cl2CoNP2; hydrogen; sodium triethylborohydride In 1,4-dioxane at 80℃; for 6h; | |
74% | With ammonia; hydrogen; nickel In methanol; water | |
74% | With ammonia; hydrogen In methanol; water | A Naphthalene-2-carbonitrile (5.57 g, 36.4 mmoles) was hydrogenated in the presence of Raney Nickel in methanol and aqueous ammonia. The solution was concentrated under reduced pressure to a red semi-solid that was purified on silica gel (EtOAc:MeOH (4:1)), combined and concentrated under reduced pressure to a light pink solid (naphthalene-2-yl-methylamine (4.21 g, 74%). |
74% | With C25H19N3ORuS; potassium <i>tert</i>-butylate In iso-butanol at 120℃; for 0.5h; Inert atmosphere; | 2.3. Transfer hydrogenation of nitriles General procedure: A flask (25 mL) containing ruthenium(II) complex (1 M%) and 2-butanol (5 mL) was stirredfor 5 min under an argon atmosphere at room temperature. Afterwards, KOtBu(0.05 mM) was added and the mixture was stirred for another 5 min. Then, the nitrile(0.5 mM) was added and placed on a hot plate at 120 °C for 30 min. After completion ofthe reaction, the catalyst was removed from the reaction mixture by addition of petroleumether followed by filtration and subsequent neutralization with 1 M HCl. The ether layerwas filtered through a short path of silica gel by column chromatography. To the filtrate,hexadecane was added as a standard and the yield was determined by GC. |
38% | With lithium aluminium tetrahydride; 1,2,3-trimethoxy glycerol ether at 0 - 20℃; Inert atmosphere; Green chemistry; | |
With palladium on activated charcoal; ethanol Hydrogenation; | ||
With lithium aluminium tetrahydride | ||
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; | ||
Multi-step reaction with 2 steps 1: ammonium sulfide / 35 - 40 °C / im geschlossenen Gefaess 2: zinc; alcoholic hydrochloric acid / 30 - 40 °C | ||
Stage #1: 2-naphthalenecarbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0 - 5℃; | 26 Reference Example 26 Tetrahydrofuran solution of 15.3 g of 2-naphthonitrile was dropped slowly to the mixture of 7.58 g of lithium aluminum hydride and 100 ml of tetrahydrofuran, and it was stirred at room temperature for 3 hours. Then the reaction mixture was cooled to 0 to 5 °C, and aqueous caustic soda was dropped slowly to it. After dropping, the mixture was filtered and filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, and separated into two layer. The organic layer was dried by magnesium sulfate, and concentrated under reduced pressure. The residue was washed by hexane to obtain 12.5 g of C-naphethalene-2-yl-methylamine.1H-NMR (CDCl3, TMS) δ (ppm): 7.80-7.83 (3H, m), 7.74 (1H, s), 7.41-7.49 (3H, m), 4.03 (2H, s), 1.62 (2H, br.s) | |
Stage #1: 2-naphthalenecarbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0 - 5℃; | ||
Stage #1: 2-naphthalenecarbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0 - 5℃; | 28 Production Example 28 [production example for the compound (I-28)]; 7.58 g of lithium aluminium hydride and 100 ml of tetrahydrofuran were mixed. Tetrahydrofuran solution of 15.3 g of 2-naphthonitrile was dropped slowly to it, and then the mixture was stirred at room temperature for 3 hours. After that the reaction mixture was cooled to 0 to 5 °C. Then aqueous solution of caustic soda was dropped slowly to the reaction mixture. After dropping the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the residue and separated to two layer. The organic layer was dried by magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane to obtain 12.5 g of 2-(aminomethyl)naphthalene.1H-NMR (CDCl3, TMS) delta (ppm): 7.80-7.83 (3H, m), 7.74 (1H, s), 7.41-7.49 (3H, m), 4.03 (2H, s), 1.62 (2H, br.s) 0.25 g of N-{(naphthalene-2-yl)methyl}-3-{3-methoxy-4-(2-propynyloxy) phenyl}propanamide was obtained by making 0.30 g of 3-{3-methoxy-4-(2-propyonyloxy)phenyl}propionyl chloride react with 0.19 g of 2-(aminomethyl)naphthalene and 0.5 ml of triethylamine.1H-NMR (CDCl3, TMS) delta (ppm): 7.76-7.82 (3H, m), 7.60 (1H, s), 7.44-7.49 (2H, m), 7.29-7.29 (1H, m), 6.89-6.90 (1H, m), 6.71-6.95 (2H, m), 5.74 (1H, br.s), 4.69 (2H, d, J=2.2 Hz), 4.55 (2H, d, J=5.9 Hz), 3.78 (3H, s), 2.96 (2H, t, J=7.6 Hz), 2.46-2.54 (3H, m) | |
78 %Chromat. | With C26H41Br2FeNP2; hydrogen; potassium hexamethylsilazane; sodium triethylborohydride In tetrahydrofuran at 140℃; for 36h; High pressure; | |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h; Reflux; | General procedure: To a stirred solution of 13, 10k or 10m (130 mmol) in dried THF (150 mL) cooled in an ice-waterbath was added portionwise LiAlH4 (6.41 g, 169 mmol). Thereafter the reaction mixture was stirredat room temperature for 1 h and then at reflux for another 5 h, when the reaction completed asindicated by TLC analysis. On cooling to room temperature, the reaction mixture was carefullypoured into ice-water (500 mL) while stirring, and the resulting mixture was diluted with CH2Cl2(300 mL), stirred for 0.5 h and filtered off through Celite. The organic phase was separated from thefiltrate, and the aqueous phase was back-extracted with CH2Cl2 (200 mL × 2). The combined organicphases were washed with saturated brine (200 mL), dried (Na2SO4) and evaporated on a rotaryevaporator to give a residue, which was purified by column chromatography through a short silicagel column to afford 2d, 2k or 2m. These amines were used directly in the next step without furtherpurification and characterization. | |
94.5 %Chromat. | With ammonium hydroxide; hydrogen In methanol for 6h; Autoclave; Heating; | |
Multi-step reaction with 2 steps 1: C16H11BrMnN3O3 / tetrahydrofuran / 24 h / 120 °C / Inert atmosphere; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C | ||
With lithium aluminium tetrahydride at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 130℃; for 2.5h; | General procedure: Benzonitrile 1a (1 mmol), Na2S*9H2O (1.2 mmol) and DMF (1 mL) were added into a 10 mL bottle. The reactor was placed in a heating magnetic stirrer at 130 C. After 2.5 h, by adding about 3 mL H2O after the reaction to disperse the solid product, the reaction mixture was extracted with EtOAc (3 x 3 mL), and the mixture was purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon disulfide; bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydroxylamine hydrochloride; triethylamine; In water; at 25℃; for 6h;Green chemistry; | General procedure: A mixture of aryl nitrile 1a-g (20 mmol), hydroxylamine hydrochloride (2.08 g, 30 mmol) and triethylamine (4.46 mL, 32 mmol) in 40 mL distilled water was stirred at room temperature (25 C) for 6 h. After completion of the reaction (monitored by TLC), the products of 2b-g were filtered, washed with distilled water, dried and used without further purification. But in the case of benzamidoxime 2a, it was extracted from the reaction mixture using ethyl acetate (3 * 30 mL), the organic layer was then dried over anhydrous MgSO4, filtered and evaporated by using a rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (6 :1) as eluent. |
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; at 50℃; | A solution of Naphthalene-2-nitrile (300 mg, 1.95 mmol) and hydroxylamine hydrochloride (164 mg, 2.35 mmol) in ethanol (6 mL) was treated with DIEA (683 muL, 3.91 mmol). The reaction mixture was heated at 50 C. overnight before it was concentrated and the crude product, N-hydroxy-naphthalene-2-carboxamidine, was used in the next step without further purification. | |
With hydroxylamine hydrochloride; potassium carbonate; In methanol; for 2h;Inert atmosphere; Reflux; | To a solution of 2-naphthonitrile 1 (1 eq.) in dry MeOH, (0114) K2CO3 (1.5 mol eq.) and hydroxylamine hydrochloride (2.5 mol eq.) were added, and the mixture was stirred at reflux for 2 h, under a nitrogen atmosphere. The resulting solution was then concentrated under vacuum, diluted with water and extracted with CH2CI2. The organic phases were dried (Na2SC>4) , filtered and concentrated in vacuo to give amidoxime 2 in quantitative yield, that were subjected to next step without any purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: NaOtBu (98% purity, 353 mg, 3.6 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 3.27 mL, 3.4 mmol) at 0 C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl benzoate (150.06 mg, 2.0 mmol) in THF (4 mL) was added to the solution at 0 C, and the obtained mixture was stirred for 4 h. Finally, aq NH3 (concentration: 28.0%-30.0%, 4 mL) and I2 (2.08 g, 4.1 equiv) were added at 0 C, and the obtained mixture was stirred for 3 h at room temperature. Then the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1) to afford benzonitrile (156.7 mg, 76% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; acetonitrile; at 20℃; for 0.666667h;Inert atmosphere; | Nitrogen protection, in a 100 mL three-necked flask equipped with a thermometer,Add anhydrous acetonitrile (10 mL) in turn, twoJia Ya satire (0·03mmol, 2·5mg, 0·Olequiv),2-naphthylcarboxamide (3mmol, 513mg, 1 · Oequiv)And triethylamine (1 · 04mL, 7 · 5mmol, 2 · 5equiv),Slowly add oxalyl chloride to the constant pressure dropping funnel at room temperature(0.31 mL, 3.6 mmol, 1.2 equiv) in dry acetonitrile (5 mL).After the addition was completed, stirring was continued for 40 min, suction filtration, and the filtrate was spun dry.Distilled water (15 mL) was added and extracted with ethyl acetate (3 chi 10 mL).The combined organic layers were washed with aq.Filtration, rotary distillation to remove the solvent to obtain a crude product.Purified by column chromatography (petroleum ether / ethyl acetate = 9:1),441 mg of 2-naphthonitrile was obtained in a yield of 96%. |
84% | at 300℃; for 1h; | General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), the stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is almost complete. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic proteomics and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10 and A-11 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99%).In these nitrile product preparation examples, 10 g of diphosphorus pentoxide was optionally added to the reaction vessel as a catalyst at the start of the reaction. |
61% | With triethylamine; ethanaminium,N-(difluoro-lambda4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In toluene; at 20℃; for 4h;Inert atmosphere; | General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: A mixture of arylnitrile (2.0 mmol) and WR (1.07 g, 2.0 mmol) in 20 mL of dry toluene was refluxed for 8 h. Upon cooling to 90C 1.0 mL of water was added, the mixture was refluxed for another 1 h. After cooling to room temperature the reaction mixture was concentrated to ca. 5.0 mL and extracted with dichloromethane (20 mL x 3), the combined dichloromethane extracts were dried over MgSO4. The final residue was purified by silica gel chromatography (9 : 1 ethyl acetate /dichloromethane as eluent) to give the compounds 1a-1i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [Ru(CO)(pyridoxalthiosemicarbazone hydrochloride)(triphenylphosphine)2]; In neat (no solvent); at 80℃; for 3h;Catalytic behavior; | General procedure: A mixture of nitrile (1.0 mmol), ethylenediamine (2.0 mmol) and catalyst (4 mol%) were heated under solvent-free conditions with stirring at 80C. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography to provide the desired product. The products were characterized by elemental analyses, 1H NMR [49],31C NMR and ESI-MS spectra. 2.6.8 : 2-naphthalen-2-yl-4,5-dihydro-1H-imidazole; Anal. Calc. for C13H12N2 (196.25 g, mol-1): C, 79.56; H, 6.61; N, 14.27%. Found: C, 79.23; H, 6.82; N, 14.53%. 1H NMR (DMSO-d6, delta): 7.32-7.92 (m, 7H, aromatic CH), 4.70 (s, 1H, NH), 4.46-4.53 (t, 2H, CH2), 4.20-4.24 (t, 2H, CH2). ;13C NMR (DMSO-d6, delta): 165.0, 136.2, 134.8, 133.1, 129.9, 128.7, 128.4, 125.3, 125.0, 53.9, 36.1. ESI-MS, m/z: 196.0 [M]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide; In dimethyl sulfoxide; at 100℃; for 24h; | General procedure: To a 100 mL eggplant type Schlenk flask were added CuBr2 (67.0 mg, 0.3 mmol), corresponding amine (3 mmol) and a solution of NMI (73.8 mg, 0.9 mmol) in DMSO (6 mL). The flask was evacuated and purged with oxygen for three times before the flask was attached to a balloon filled with oxygen. Then the flask was heated at 100 C for 24 h. After the flask was cooled down and the reaction mixture turned into green color, water (15 mL) and dichloromethane (15 mL) was added into the mixture. The water layer was extracted with dichloromethane (5 mL x 3) and the organic layers were combined. After removing the solvent, residue was purified by column chromatography (PE/EA = 100:1) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride; In water; acetonitrile; at 20℃; for 24h; | General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 mol%), DABCO (0.10 mol, 10 mol%), 4-HO-TEMPO (0.05 mmol, 5 mol%) were added. Substrates 1 (1 mmol) and NH3 (aq, 25-28%, 3 mmol, 3.0 equiv) in CH3CN (2 mL) were added subsequently. Then the reaction mixture was stirred at room temperature for 24 h in the presence of an air balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding products. |
74% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid; acetic acid; at 50℃; under 760.051 Torr; for 12h;Sealed tube; | General procedure: 0.5 mmol substrate, 1.5 mmol NH4OAc, 0.15 mmol TEMPO, 2 mL AcOH and 0.15 mmol HNO3 weresuccessively added to a dried 45 mL tube filled with 1atm oxygen. Then the reaction tube was sealed andplaced in a constant-temperature oil bath to perform the reaction for 12 h. Once the reaction time wasreached, the mixture was cooled to room temperature. Then the mixture was alkalized to pH 7-8 with sodiumhydroxide aqueous solution. GC analysis of organic phase provided the GC yields of the products.Subsequently, the crude product from another parallel experiment was purified by column chromatography,and identified by 1H-NMR, 1C-NMR or GC-MS |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-naphthalenecarbonitrile; ethylmagnesium chloride In diethyl ether at 20℃; for 21h; Heating / reflux; Stage #2: With hydrogenchloride In diethyl ether; water | 2 Preparation 2: l-Νaphthalen-2-ylpropan-l-one2-Naphthonitrile (3g, 19.6mmol) was dissolved in Et2O (2OmL) followed by addition of ethylmagnesium chloride (2.0M in Et2O, 9.8mL, 19.6mmol) and the reaction was heated to reflux for 5hr, then stirred at rt for 16hr. The reaction was quenched with 2N HCl (2OmL) and water (2OmL) then extracted into DCM (3 x 4OmL). The combined organic fractions were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with EtOAc:hexanes (1:9) to afford the title compound, δϖ (CDCl3): 1.30 (3H, t), 3.13 (2H, q), 7.57 (2H, m), 7.88 (2H, m), 7.96 (IH, d), 8.05 (IH, dd), 8.47 (IH, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example b.; Step a:; LiAlH4 (0.4 g, 10 mmol) was added to naphthylnitrile (1.55 g, 10 mmol) in anhydrous THF at 0 C. in portions and mixture was stirred for 1 hr. The reaction was quenched with MeOH and then washed with water. The organic layer was then extracted with 1 N HCl. The aqueous solution was left to stand for 24 hr. at 4 C. to yield crystal of the desired amine. | ||
General procedure: A solution (50 mL) containing the nitrile (5 mmol), and dichloro(p-cymene)ruthenium(II) dimer (0.05mmol) in 2-propanol (solution was sonicated until the catalyst was solubilized 10-50 min) was pumpedat 4 mL/min through the reactor coil heated at 200 C. The Phoenix backpressure regulator was set tomanual at 30%, which correlated to approximately 100 bar. A 10 mL fraction of the solution obtainedfrom the system in steady state was used to prepare the hydrochloric salt by method A or B dependingon substrate. Yields are reported as isolated hydrochloride salts, unless otherwise stated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium azide; In N,N-dimethyl-formamide; at 110℃; for 4h; | General procedure: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 mol%) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 × 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 × 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium azide; N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 4h; | |
90% | With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 120℃; for 22h; Green chemistry; | |
75% | With iron(III) trifluoromethanesulfonate; sodium nitrite In dimethyl sulfoxide at 50℃; for 10h; Inert atmosphere; Sealed tube; | Nitriles 2a-r: General Procedure General procedure: A tube of approximate volume 45 mL was charged with theappropriate arylacetic acid (0.5 mmol), NaNO2 (3 mmol),Fe(OTf)3 (1 mmol), and undried DMSO (2 mL), and the air in thetube was replaced by argon gas. The tube was sealed and themixture was heated with magnetic stirring at 50 °C for 10 h,then cooled to r.t. The solvent was evaporated, and the residuewas purified by column chromatography (silica gel). |
65% | With 1,10-Phenanthroline; oxygen; copper(II) oxide; potassium ferrocyanide In dimethyl sulfoxide at 120℃; for 40h; Autoclave; | 2.2. General procedure for the conversion of arylacetic acids to aromatic nitriles General procedure: The reaction was carried out in a 40 mL stainless steel autoclave lined with Teflon. Typically, 0.5 mmol substrate, 0.6 mmol K4Fe(CN)6, 0.1mmol CuO, 0.5 mmol 1,10-phenanthroline and 2 mL DMSO were added into the reactor and 1.5MPa of oxygen was filled. Then the reaction system was heated under magnetic stirring at 120°C for 40h. Once the reaction time was reached, the mixture was cooled to room temperature. GC analysis of the reaction mixture provided the GC yields of the products. In addition, the crude product from another parallel experiment was purified by column chromatography, and identified by 1H NMR and 13C NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With copper (II)-fluoride; bis(tricyclohexylphosphine)nickel(II) dichloride; potassium <i>tert</i>-butylate; tricyclohexylphosphine In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: 2-naphthalenecarbonitrile; methylmagnesium bromide In tetrahydrofuran; diethyl ether at 100℃; for 0.166667h; Microwave irradiation; Stage #2: With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 50℃; for 1h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; In decane; acetonitrile; at 0℃; for 6h; | Representative procedure: To a solution of 1-(azidomethyl)-4-methoxybenzene (8a) (81 mg, 0.5 mmol) in MeCN (0.5 mL) was added PhI(OAc) (1) (483.1 mg, 1.5 mmol) at 0 C. The resultant suspension was stirred vigorously while a solution of tBuOOH (2) (5.0-6.0 M in decane, 360 muL, 2.0 mmol) was added dropwise over 1 h. After the addition, the reaction mixture was stirred for 11 h followed by chromatography on silica gel with n-hexanes/EtOAc (10:1) to yield 4-methoxybenzonitrile (9a) as a yellow oil (55.3 mg, 83%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: n-Butyllithium (1.67 M solution in hexane, 3.3 mL, 5.5 mmol) was added dropwise to a solution of p-bromotoluene (855 mg, 5.0 mmol) in THF (5 mL) at -70 C. After 30 min, the resulting mixture was warmed and stirred for 5 min at 0 C. Then, DMF (0.43 mL, 5.5 mmol) was added and the obtained mixture was stirred at 0 C. After 1 h at the same temperature, aq NH3 (10 mL, 150 mmol) and I2 (1.40 g, 5.5 mmol) were added and the obtained mixture was stirred for 2 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (15 mL) and extracted with Et2O (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide 4-methylbenzonitrile in over 80% purity. The product was purified by a short column chromatography on silica gel (Hexane/EtOAc=9:1) to give pure 4-methylbenzonitrile in 80% yield as a colorless solid. | |
65% | General procedure: To a flask containing Mg turnings (0.28 g, 14 mmol) was added p-bromotoluene (1.38 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL, 12 mmol) was added to the reaction mixture. The obtained mixture was stirred for 2 h at room temperature. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 1.6 mmol) were added to the reaction mixture. After being stirred overnight, the reaction mixture was poured into aq sat. Na2SO3 solution and extracted with CHCl3 (3 × 30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue was purified by short column chromatography on silica gel (eluent: hexane / ethyl acetate = 9:1, v/v) to provide pure p-tolunitrile (0.77 g) in 67% yield. Most aromatic nitriles mentioned in this work are commercially available and were identified by comparison with the authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | General procedure: To a solution of N,N-dimethyl benzamide (298 mg, 2 mmol) in dry THF (4 mL) was added DIBAL-H (1.04 M in hexane, 2.3 mL, 1.2 equiv) at -78 C. The mixture was stirred for 1.5 h under an argon atmosphere at from -70 C to -40 C slowly. Then, aq NH3 (concentration: 28.0-30.0%, 4 mL) and I2 (762 mg, 3.0 equiv) were added at 0 C, and the reaction mixture was stirred for 2 h at room temperature. Reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by short column chromatography on silica gel (eluent: hexane/ethyl acetate=4:1) to afford benzonitrile in 67% yield (138 mg).Most of the present prepared nitriles are commercially available and they are identified with authentic nitrile compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 10% CuO-ZnO on activated carbon; In toluene; at 100℃; for 4h;Inert atmosphere; | General procedure: Calculated amount of catalyst (for example 60 mg), benzaldehyde oxime 4 (670 mg) and 1.1 mL toluene as a solvent were taken in an oven-dried, nitrogen purged Schlenk tube. Then the mixture was purged with nitrogen and stirred at 100 °C for 4 h. After set reaction time, the mixture was allowed to cool to room temperature, diluted with 2 mL ethanol, and filtered. The analysis of filtered reaction mixture was carried out by gas chromatography (Varian 3900) equipped with CP-Sil 5CB capillary column (15 m length and 0.25 mm diameter) and a flame ionization detector (FID). GC oven temperature was programmed from 60 to 110 °C at the rate of 8 °C/min and 111 to 300 °C at the rate of 25 °C/min. Helium was used as a carrier gas. Temperatures of injection port and FID were kept constant at 295 and 300 °C, respectively. Retention times of different compounds were determined by injecting pure compound under identical conditions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cis-[NiCl2(PPh3)2]; potassium <i>tert</i>-butylate In 1,4-dioxane at 90℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; potassium tert-butylate; triethylamine; bis(dibenzylideneacetone)-palladium(0); In dichloromethane; water; acetonitrile; at 50℃; for 24h;Inert atmosphere; | General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 mol%) and ligand L4 (8.4 mg, 0.02 mmol, 2 mol%). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL × 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization |
82% | With sodium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 20h; | A round-bottomed flask (10 mL) was charged with 2-bromonaphthalene(1.5 mmol, 0.311 g), Na2CO3 (1.8 mmol, 0.190 g), the catalyst (0.0075 g, 1.7 mol%) and 1:1 (V/V) DMF/H2O (5 mL). The reaction mixture was heated to 120 C and K4[Fe(CN)6].3H2O (0.60mmol, 0.253 g) was then added. The final mixture was stirred for 20 h. at 120 C. After allowing the mixture to cool to room temperature, the catalyst was filtrated.Then H2O (15 mL) was added to the mixture and the product was extracted with ethyl acetate (3 10 mL). The organic extracts were collective and dried over anhydrous Na2SO4. Evaporation of the solvent afforded the crude desired product, which was purified by column chromatography using hexane/EtOAc 25:5 (v/v) as the eluents, to afford the title compound.The spectral data for this compound corresponds to those reported in the literature. Yield: 82%. White solid.M.p. 65-67oC.1H-NMR (300 MHz, CDCl3/TMS) delta (ppm): 7.50-7.59 (m, 3H), 7.79-7.85 (m, 3H), 8.14-8.15 (m, 1H). Anal.Calcd.forC11H7N (153.18): C, 86.25; H, 4.61; N, 9.14. Found: C, 86.18; H, 4.54; N, 9.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / diethyl ether / 5 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: ethanol / Inert atmosphere; Reflux 3.1: sodium methylate / toluene / 0.33 h / Inert atmosphere 3.2: 13 h / 60 °C / Inert atmosphere 4.1: hydrogenchloride; zinc / ethanol; water / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / diethyl ether / 5 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: ethanol / Inert atmosphere; Reflux 3.1: sodium methylate / toluene / 0.33 h / Inert atmosphere 3.2: 13 h / 60 °C / Inert atmosphere 4.1: hydrogenchloride; zinc / ethanol; water / 20 °C / Cooling with ice 5.1: ethanol / 20 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With formic acid; sodium nitrite; In acetonitrile; at 70℃; for 4h;Schlenk technique; | General procedure: A Schlenk tube was charged with olefins 1 (0.4 mmol), NaNO2 (138 mg, 2 mmol), HCOOH (0.5 mL, 10 mmol), and CH3CN(4.5mL). The reaction mixture was stirred at 70 C under air atmosphere for 4 h. After cooling to room temperature, the solution was filtered to remove the solid by-product then was washed with ethyl acetate (3×10 mL). The solution was concentrated under vacuum and purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate) to obtain the desired product 2. |
81.3% | With formic acid; 5,10,15,20?tetrakis?(4?sulfonatophenyl)?porphyrin?iron(III) chloride; sodium nitrite; In acetonitrile; at 70℃; for 4.5h; | To the reaction tube was added 0.4 mmol of 2-vinylnaphthalene, 2 mmol of sodium nitrite,3 mg of metallic iron (III) porphyrin and 4.5 ml of acetonitrile solvent were added, heated and stirred at 70 C in an air atmosphere,0.5 ml of formic acid was added dropwise within the first 0.5 hours, after reacting for 4 hours, heating and stirring were stopped,After cooling to room temperature, the crude product was obtained by rotary evaporator and then purified by column chromatography,The target product was obtained. The column eluant used was a mixed solvent of petroleum ether and ethyl acetate.The 2-cyanonaphthalene structure is shown below:The compound was a white solid in a yield of 81.3% and its nuclear magnetic data was as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With di-tert-butyl{2?-isopropoxy-[1,1?-binaphthalen]-2-yl}phosphane; palladium diacetate; potassium carbonate; phenylboronic acid; In water; tert-butyl alcohol; at 100℃; for 6h;Inert atmosphere; Schlenk technique; | General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(OAc)2 (4.5 mg, 0.02 mmol ), L1 (36.5 mg, 0.08 mmol), PhB(OH)2 (6.1 mg, 0.05 mmol), and t-BuOH (2 mL), and the mixture was stirred for half hour at 50 C. After cooling to r.t., aryl chloride or mesylates (1.00 mmol), K4[Fe(CN)6]·3H2O (211.2 mg, 0.50 mmol), K2CO3 (138.2 mg, 1.00 mmol), and H2O (2 mL) were added. The septum was replaced with an inside reflux condenser, and then the Schlenk tube was placed in an oil bath preheated to 100 C (120 C for aryl mesylates) with stirring for 6 h (24 h for aryl mesylates). Then the reaction mixture was allowed to cool to r.t., extracted with CH2Cl2, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium phosphate; In N,N-dimethyl-formamide; at 120℃; for 2h; | General procedure: Aryliodide (0.5 mmol), K4[Fe(CN)6]3H2O(0.15 mmol), K3PO4 (1.5 mmol) and Pd-BNP (5.3 mg, 0.005 mmol, 1.0 mol%)were taken in a oven dried reaction tube equipped with magnetic pellet. DMF(2.0 mL) was added to the reaction tube and the reaction mixture was stirred at120 C temperature. The reaction was monitored by TLC. After consumption ofthe starting material, the reaction mixture was cooled to room temperature.Crude product was extracted with ethyl acetate (3 10 mL). Then the organicphase was dried over Na2SO4 and concentrated in vacuum. The product waspurified by column chromatography using silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile (5b, 124.6 mg, 0.928 mmol) in 86% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 24h; | 4-Alkoxy-2-oxazolines; General Procedure General procedure: To a solution of the appropriate nitrile (0.31 mmol) in anhyd DCE (1 mL) was added TfOH (44 μL, 0.49 mmol) and GADA (47 μL, 0.46 mmol). After stirring at r.t. for 24 h, the reaction mixture was poured into H2O and adjusted to pH 8 with sat. aq NaHCO3, which was then extracted with CH2Cl2 (3 ×). The organic layers were combined and washed with H2O and brine, dried over anhyd Na2SO4, and concentrated in vacuo to give the product. The crude product was purified by a silica gel column (PE/EtOAc = 10:1-3:1, v/v), unless stated otherwise. The significant loss of product was due to the difficulty in isolation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With tert.-butylhydroperoxide; copper(l) iodide In N,N-dimethyl-formamide at 130℃; for 24h; | General procedure for the preparation of substituted benzonitriles (3a-3u) General procedure: To a 25 mL round flask was added the mixture of boronic acid (1) (0.3 mmol), ethyl2-cyano-3-ethoxyacrylate (2a, 0.6 mmol), CuI (0.3 mmol), t-BuOOH (0.6 mmol) in DMF (2 mL)successively. The mixture was stirred at 130 °C for 24 h under air. After the reaction was completed, themixture was cooled to room temperature, diluted with water (15 mL) and then extracted withdichloromethane (5 mL × 3). The organic extract was washed with H2O (10 mL × 3) and dried overanhydrous Na2SO4. After removal of the CH2Cl2 in vacuum, the crude product thus obtained was purified bycolumn chromatography on silica gel using petroleum ether/ethyl acetate as eluent to give the desired product3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium phosphate; nickel dibromide; zinc; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; copper(II) trifluoroacetate In dimethyl sulfoxide at 120℃; for 22h; Sealed tube; Green chemistry; | 12.1 General procedure: phenylacetic acid or its derivative (0.5mmol), Cu(TFA)2(20mmol%), urea (1.5 mmol) was added to the pressure sealed tube containing (0.75mL) of DMSO, after filling oxygen at 130 stirred for about 20h, the process by TLC and GC tracking (specifically the reaction time is determined by GC and TLC tracking results). After the raw material was observed by the GC and TLC the reaction has been completed the reaction, the reaction was removed, cooled to room temperature.To the reaction was added 20mL of ethyl acetate, washed with NaHCO3(20mL × 2), washed with saturated brine 20mL.The combined aqueous phases with ethyl acetate (20mL × 2) after stripping the combined organic phases with anhydrous sodium sulfate. The organic phase was dried by rotary evaporator spin solvent, product was purified by silica gel column, eluent ratio of ethyl acetate: petroleum ether = 50: 1. Benzonitrile obtained in a yield of 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium t-butanolate In toluene at 120℃; for 12h; | |
69% | With cesiumhydroxide monohydrate In 1,4-dioxane at 100℃; for 24h; Schlenk technique; | |
67% | With C39H32Cl2N5PRu; potassium <i>tert</i>-butylate In tert-Amyl alcohol at 130℃; for 2h; Sealed tube; | 4.2. General procedure for preparation of quinazolines 3 or 4 General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4. |
69 %Chromat. | With cesium hydroxide In 1,4-dioxane at 100℃; for 24h; | 16 Example 16: O-aminobenzyl alcohol(2-naphthyl) quinazoline with 2-naphthalenecarbonitrile A tubular reactor was charged with o-aminobenzyl alcohol (0.123 g, 1 mmol),2-naphthalenecarbonitrile (1.25 mmol, 1.25 equiv.)And cesium hydroxide (0.149 g, 100 mol%) were placed under direct air flow. The air spheres were connected with each other and heated to 100 ° C for 24 h.After TLC monitoring was complete, the product was isolated by column chromatography and the yield was 69%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc; In acetonitrile; at 50℃; for 11h;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 88%, and 1H NMR purity was greater than 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With C29H28Cl2N2Ti; In neat (no solvent); at 65℃; for 12h;Inert atmosphere; Schlenk technique; Glovebox; | General procedure: Catalyst 1 (10 mol%) and HBpin (0.44 mmol) were added to aSchlenk flask inside the glove box, followed by the addition oforganic nitriles (0.2 mmol). The reaction mixture was heatedcontinuously at 65 C under neat condition or under toluene for astipulated time, as mentioned in Table 2. Toluene was then added,and the reaction mixture was filtered through a short plug of Celiteand evaporated under reduced pressure to obtain a solid residue.The diboryl amines are moisture- and air-sensitive, and henceexperimental procedures were conducted and NMR samples wereprepared inside the glove box. All products were characterizedusing multi-nuclear NMR spectroscopy, and details are given in thesupporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cerium(III) chloride In tetrahydrofuran at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With C39H32Cl2N5PRu; potassium tert-butylate; In tert-Amyl alcohol; at 130℃; for 10h;Sealed tube; | General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With cesium fluoride; lithium hexamethyldisilazane; In 1,4-dioxane; at 110℃; for 12h;Green chemistry; | General procedure: Lithium bis(trimethylsilyl)amide (66.8 mg, 0.4 mmol) and cesium fluoride (30.4 mg, 0.2 mmol) were placed in a microwave tube in a glove box. Add 0.4 mL of cyclopentyl methyl ether, Then <strong>[95-52-3]2-fluorotoluene</strong> (66 muL, 0.60 mmol) and benzonitrile (20 muL, 0.20 mmol) were added separately using a micro syringe. which was taken out from the glove box and refluxed at 110 C for 12 hours. After cooling to room temperature, the reaction was capped and three drops of water were added to quench the reaction. The solvent was removed under reduced pressure and the crude product was purified by column chromatography ( petroleum ether: ethyl acetate = 20:1) to give 2-phenylindole (34.7 mg) , 90% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85.1% 2: 14.9% | With ammonium hydroxide; hydrogen In hexane at 80℃; for 18h; Autoclave; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 180℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; | Method B: Palladium-catalyzed Cyanation of Acyl Chlorides by Trimethylsilyl Cyanide (3b,Table 3) General procedure: In a glovebox filled with nitrogen, Pd2(dba)3*CHCl3 (23.8 mg, 0.023 mmol), Xantphos (34.1 mg,0.059 mmol), 4b (69.6 mg, 0.45 mmol) and 2 (67.5 mg, 0.68 mmol) were added to a 10 mL-samplevial with a Teflon-sealed screwcap. Toluene (1.5 mL) was then added, and the vial was then sealedwith the cap. The vial was stirred at 180 °C for 24 h. After allowing the reaction mixture to cool toroom temperature, diisopropylamine was added to the crude mixture and filtered through a pad ofsilica gel and the pad was washed with EtOAc. The filtrate was analyzed by GC using dodecane asan internal standard. |
80% | With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 110℃; for 1h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl isocyanide In tetrahydrofuran; hexane at -50 - 20℃; for 0.5h; Inert atmosphere; Further stages; | 4.2. Typical procedure (1): transformation of 4-bromobiphenyl 1a into 4-cyanobiphenyl 2a General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 °C. The obtained mixture was stirred for 30 min at 50 °C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 °C and the obtained mixture was stirred for 30 min in the temperature range of 50 °C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 °C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With copper nitrate hemi(pentahydrate); 4,4'-bis(carbomethoxy)-2,2'-bipyridine; sodium amide In N,N-dimethyl-formamide at 130℃; for 15h; | 2. Typical experimental procedure for the cyanation of aryl iodides General procedure: Under air atmosphere, a reaction tube was charged with aryl iodides (0.5 mmol), Ph3P+CF2CO2- (268 mg, 0.75 mmol, 1.5equiv), L4 (6.3 mg, 5 mol %), Cu (NO3)2·2.5H2O (143 mg, 0.65 mmol, 1.3 equiv), NaNH2 (39 mg, 1.0 mmol, 2.0 equiv) and dry DMF (4 mL). The resulting mixture was stirred at 130°C for 15 h. After being cooled to room temperature, the mixture was filtered through a pad of Celite. The solid was washed with DCM, and the combined organic phase was washed with water (15 mL × 3). The organic layer was further washed with saturated sodium sulfite and saturated brine, and then dried with sodium sulfate. After the solvent was removed by concentration under vacuum, the residue was subjected to flash column chromatography to afford the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With copper orthophosphate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Sealed tube; | 3.3 General experimental procedure for products 3a - 3y using 3a as an example (General Procedure C) General procedure: To a sealing tube (10 mL) were added the aryl iodide 1a (0.5 mmol, 1 equiv), the substrate 2a (1.0 mmol, 2 equiv), and the solvent DMF (2 mL) at room temperature under argon atmosphere. After the dissolution of above reactants, the catalyst Cu3(PO4)2 (0.1 mmol, 0.2 equiv) was added. Next, the reaction mixture was sealed and heated at 120 °C until the reaction was completed (monitored by TLC). The reaction mixture was quenched by water. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with brine (50 mL), dried over sodium sulfate and concentrated under vacuum. The residue was purified using flash column chromatography (petroleum ether/ether,30 : 1) to give the desired products. |
96% | With copper orthophosphate In N,N-dimethyl-formamide at 120℃; Sealed tube; Inert atmosphere; | 24 24. Using 2-iodonaphthalene as raw material (reaction formula 24) To a sealed tube (10 mL) was added 2-iodonaphthalene (127 mg, 0.5 mmol), 2-(dimethylamino)malononitrile (109 mg, 1.0 mmol) and solvent DMF (2 mL) at room temperature under argon . After the dissolution of the above reactants was completed, the catalyst Cu3(PO4)2 (38 mg, 0.1 mmol) was added. The reaction mixture was sealed and heated at 120°C until the reaction was complete. The reaction mixture was quenched with water, the aqueous layer was extracted with EtOAc, and the combined organic layers were washed with saturated brine (50 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified using flash column chromatography to give a white solid (73.4 mg, 96% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium bicarbonate; copper(II) nitrate In dimethyl sulfoxide at 140℃; for 30h; Autoclave; | Representative Procedure for Conversion of Various Arylethenesto Aromatic Nitriles General procedure: To a stainless steel autoclave lined with Teflon, 0.5 mmol substrate,0.075 mmol Cu(NO3)2, 1 mmol (NH4)2CO3, and 2 mLDMSO were added. Then the reactor was filled with 2 MPaoxygen and was heated under magnetic stirring at 140 °C for 30h or 40 h (Caution: the use of the high-pressure oxygen ispotentially hazardous. Thus, experiments using the high-pressureoxygen must only be carried out under rigorous safety precautions,and it is required to use the appropriate high-pressurereactor to avoid the potential leakage or explosion of the gas).Once the reaction time was reached, the mixture was cooled toroom temperature, diluted with 30 mL diethyl ether, and filteredvia a Celite pad. The organic mixture was washed withwater (3 × 5 mL), dried with anhydrous sodium sulfate, and concentratedin vacuum. GC analysis provided the GC yields of theproduct with an internal standard. In addition, the combinedcrude product from another 1-5 parallel experiments was purifiedby column chromatography and identified by 1H NMR and13C NMR spectroscopy. All the products are the known compounds,and the analytical data of several typical compoundsare as follows: |
Tags: 613-46-7 synthesis path| 613-46-7 SDS| 613-46-7 COA| 613-46-7 purity| 613-46-7 application| 613-46-7 NMR| 613-46-7 COA| 613-46-7 structure
[ 2920-38-9 ]
[1,1'-Biphenyl]-4-carbonitrile
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[1,1'-Biphenyl]-4-carbonitrile
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