| 99% |
With manganese(IV) oxide; lithium hydroxide monohydrate In isopropanol at 100℃; for 0.2h; |
|
| 99% |
With C12H24O16Ru3*2H2O In lithium hydroxide monohydrate at 110℃; for 1h; Schlenk technique; Inert atmosphere; Autoclave; |
2.6. Catalytic experiments
General procedure: Hydration reactions were carried out in Schlenk tube under N2atmosphere. The reaction mixture was prepared dissolving 5 mg(6.5 lmol) of catalyst 2 in 3 mL of H2O. The mixture was degassedand 1.5 mmol of corresponding acetonitrile substrate was addedwith micropipette to stirred solution. The reaction was allowedfor heating at 110 C using oil bath or microwave-assisted heating.The isomerization reactions of allylic alcohols were conductedSchlenk tube under N2 atmosphere. The reaction mixture wasprepared dissolving 3 mg (3.9 lmol) of catalyst 2 in 2 mL ofappropriate solvent (DMF, EtOH or H2O). The mixture wasdegassed and 1 mmol of corresponding allylic alcohol substratewas added with micropipette to stirred solution. The reactionwas allowed for heating using oil bath.The reaction solutions were analyzed by regular sampling usingGC/FID (Hewlett Packard) equipped with Beta DEX 120(30 m 0.25 mm 0.25 lm) 30 m long column. The degrees ofconversion were calculated on the basis of the ratio of areas ofthe substrate material and the products determined from correspondingchromatograms. The optimization of chromatographicmethods and the calibration procedures for detection of productsas well as substrates were realized by injection of authenticcommercial samples. |
| 99% |
With C43H42Cl2NRu; lithium hydroxide monohydrate at 20℃; for 4h; |
|
| 99% |
With [RuH(tBu-PNP(-))(CO)]; lithium hydroxide monohydrate In <i>tert</i>-butyl alcohol at 20℃; for 24h; |
|
| 98% |
With lithium hydroxide monohydrate; Cs2CO3 at 150℃; for 0.25h; Microwave irradiation; |
|
| 98% |
With di-μ-chlorobis-[(η6-p-cymene)chlororuthenium(II)]; lithium hydroxide monohydrate; 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantyl chloride for 1h; Schlenk technique; Reflux; Green chemistry; |
Hydrationof nitriles to amides
General procedure: In a Schlenk-tube of approximately 12 mL volume, 0.05 mmol Ru(II)-precursor (1, 2 or RuCl3×3H2O) and 0.15 mmol phosphine ligand were dissolved in 3 mL water. This was followed by addition of 1 mmol nitrile. The tube was equipped with a reflux condenser and then immersed to an oil bath of 108-110 °C temperature. The reaction mixture was stirred magnetically under reflux on air. In case of aliphatic nitriles heavy-walled closed reaction tubes of 5 mL volume were used. At the end of the reaction (or at other appropriate reaction times) 50 μL samples were withdrawn from the hot reaction mixture and these were extracted with 3×2 mL dichloromethane. A 1.5 mL portion of the combined organic phases was passed through a plug of unhydrous MgSO4 and the resulting clear solution was analysed by gas chromatography. |
| 98% |
With [2,2]bipyridinyl; lithium hydroxide monohydrate; palladium diacetate In 1,4-dioxane at 70℃; for 24h; Schlenk technique; Sealed tube; |
General Procedure XIII - Synthesis of Primary Amide Products in Water/Dioxane
General procedure: To an oven dried Schlenk carousel tube containing the appropriate nitrile (1 mmol) was added palladium acetate (11 mg, 5 mol%), 2,2'-bipyridine (7.8 mg, 5 mol%), dioxane (0.6 mL) and water (1.4 mL). The tube was then sealed and the reaction mixture heated at 70 °C (unless otherwise stated) for 24 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with methanol (5 mL) and the solvent removed in vacuo on a rotary evaporator whilst azeotroping with toluene. Where the reaction had gone to quantitative conversion or the starting nitrile was volatile, the crude reaction mixture was passed through a short plug of silica to remove the catalyst (eluting with DCM/MeOH, 95:5). Otherwise, the primary amide products were purified by column chromatography (eluting with DCM/MeOH, 95:5, unless otherwise stated). |
| 97% |
With sodium hydroxide; dihydrogen peroxide In dichloromethane for 1.33333h; Ambient temperature; |
|
| 97% |
With manganese(IV) oxide In 1,4-dioxane at 140℃; for 1h; Inert atmosphere; |
|
| 97% |
With polystyrene-triethylenetetramine anchored ruthenium(II) complex; air In lithium hydroxide monohydrate at 90℃; for 7h; Green chemistry; |
|
| 97% |
With mPMF-Ag0 nanocatalyst In lithium hydroxide monohydrate at 90℃; for 7h; |
|
| 96% |
With lithium hydroxide monohydrate at 140℃; for 2h; Inert atmosphere; |
|
| 96% |
With N-ethyl-N-hydroxy-ethanamine; lithium hydroxide monohydrate; copper (II) acetate In ethanol at 35℃; for 3h; |
|
| 96% |
With nickel(II) oxide; potassium hydroxide In isopropanol at 40℃; Green chemistry; |
|
| 96% |
With lithium hydroxide monohydrate at 110℃; for 6h; |
2.2 General Procedure for Hydration of Nitriles to Amides
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. |
| 96% |
With lithium hydroxide monohydrate; C33H28F3N5O3Ru(1+)*Cl(1-) at 60℃; for 0.5h; Sonication; |
2.5 General Procedure for the Catalytic Hydration ofNitriles.
General procedure: The corresponding nitrile (1.0mmol), water (5.0 mL)and the ruthenium(III) catalyst 5a (0.1 mol%) were introducedinto a flask and the reaction mixture was sonicated at 60 °C forthe indicated time. The course of the reaction was monitored byTLC analysis. Once the reaction finished, the hot mixture waspassed through a filter paper (to remove the catalyst), allowedto reach room temperature, and then kept in an ice bath for 2 h.This led to the crystallization of the corresponding primaryamide, which was separated, recrystallized from hot water,washed with n-hexane (3 5.0 mL) and vacuum-dried. Theidentity of the amides was assessed by comparison of theirNMR spectroscopic data with those reported in the literature. |
| 95% |
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; lithium hydroxide monohydrate In tetrahydrofuran at 140℃; for 6h; Microwave irradiation; |
|
| 95% |
With (Ru(1,2:5,6-η-1,5-cyclooctadiene)(η(3)-methallyl)2); lithium hydroxide monohydrate; 2-(diphenylphosphino)-N,N-dimethylpyridine-4-amine In 1,2-dimethoxyethane at 80℃; for 5h; |
|
| 95% |
With Acetaldehyde oxime; copper(II) oxide In lithium hydroxide monohydrate for 10h; Reflux; |
Experimental Procedures for Hydration of Various Nitriles
General procedure: To a 25 mL round-bottom flask equipped with magnetic stirrer were added nitrile (2.5 mmol), acetaldoxime (3.75 mmol), copper oxide (0.25 mmol) and H2O (10 mL). The mixture was heated to reflux for 2-14 h. After cooling to room temperature, the solution was directly evaporated to dryness and the residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give the corresponding amides. The commercially available amides were characterised by melting points, 2-amino-5-bromobenzamide (Table 2, entry 6) and 3,4-dichloropicolinamide (Table 2, entry 13) were characterised by NMR spectra and LC-MS. |
| 95% |
With tetra(n-butyl)ammonium hydroxide In ethanol; lithium hydroxide monohydrate at 80℃; for 5h; Green chemistry; chemoselective reaction; |
|
| 95% |
With potassium-t-butoxide In <i>tert</i>-butyl alcohol at 20℃; for 5h; Inert atmosphere; |
|
| 95% |
With Caswell No. 744A; lithium hydroxide monohydrate at 90℃; for 0.5h; |
General procedure for amide synthesis
General procedure: To an aqueous mixture of nitrile (1 mmol) in water (7 mL) was added NaN3 (0.1 mmol, 0.0065 g), then the reaction mixture was stirred vigorously in an oil bath preset at 90 °C for the appropriate time as mentioned in Table 1. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled and the precipitated-outsolid was filtered and washed with water (3 × 5 mL) to give the pure product. The products were identified by their 1H NMR spectra and their physical data (m.p.) were compared with those described in the literature. Spectral data for the selected compound are as follows. |
| 95% |
With lithium hydroxide monohydrate In dimethyl sulfoxide at 100℃; Green chemistry; |
|
| 94% |
In lithium hydroxide monohydrate at 100℃; for 24h; |
|
| 94% |
With N-ethyl-N-hydroxy-ethanamine; lithium hydroxide monohydrate at 100℃; for 4h; |
|
| 94% |
With cobalt(II,III) oxide; lithium hydroxide monohydrate at 140℃; for 17.5h; |
|
| 94% |
With Cupric sulfate; hydroxyamino hydrochloride; anhydrous Sodium acetate at 110℃; for 2h; Neat (no solvent); |
|
| 94% |
With choline chloride * 2ZnCl2 In lithium hydroxide monohydrate at 100℃; for 12h; Green chemistry; |
|
| 94% |
With copper (I) iodide; nitromethane; Cs2CO3; 1,8-diazabicyclo[5.4.0]undec-7-ene In lithium hydroxide monohydrate at 100℃; for 1h; |
|
| 94% |
With 1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene silver chloride; lithium hydroxide monohydrate at 50℃; for 7.5h; |
1.3. General procedure for the synthesis of amides 2a-2x:
General procedure: Synthesis of benzamide (2a) : (0.03 mmol) of Ag(I)-NHC catalyst (3a) was added to 1 mL of H2O in 5 mL round bottom flask. To this 1 mmol of benzonitrile (1a) was added and the reaction mixture was stirred for 8 h at 50 °C. After the completion of reaction as monitored by TLC, the resulting mixture was filtered through a pad of celite and extracted with DCM (2 x 5 mL). The combined organic phase was concentrated under reduced pressure. The crude product was purified by column chromatography using a gradient of hexane/ethyl acetate (1:1). The compound 2a (91%) was isolated as a white solid. Similar procedure was followed to synthesize other amides 2b-2x. |
| 94% |
With [RuCl(η6-p-cymene)(benzyl N'-thiophene-2-carbonyl-N-(pyridin-2-ylmethyl)carbamimidothioate)]Cl; potassium hydroxide In isopropanol at 82℃; |
|
| 93% |
With C19H23Cl2N6PRuS3*3ClH; lithium hydroxide monohydrate at 100℃; for 3h; Inert atmosphere; Schlenk technique; |
|
| 93% |
With lithium hydroxide monohydrate; palladium diacetate; glacial acetic acid; scandium trifluoromethanesulphonate at 30℃; for 12h; |
|
| 92% |
With manganese(IV) oxide; lithium hydroxide monohydrate In 1,4-dioxane at 140℃; for 1h; Inert atmosphere; Autoclave; |
|
| 92% |
With lithium hydroxide monohydrate In ethanol at 50 - 60℃; for 2h; |
General Procedure for Synthesis of Primary Amides
General procedure: Amberlyst A26 OH (0.11 g) was added to a suspension ofthe nitrile (1 mmol) in EtOH-H2O (0.5 mL). The reactionmixture was stirred at 50-60 °C, and the progress of thereaction was followed by TLC. After the completion ofreaction, the mixture was diluted with acetone or EtOAc andfiltered to remove the catalyst. The desired products wereisolated by evaporation of the EtOAc or addition of H2O and filtration of the precipitate. |
| 91% |
With 1,3-dimethylimidazolium hydrogen carbonate; lithium hydroxide monohydrate In ethanol at 80℃; for 6h; Green chemistry; chemoselective reaction; |
|
| 91% |
With Acetaldehyde oxime; sodium molybdate(VI) dihydrate In lithium hydroxide monohydrate for 12h; Reflux; |
Experimental Procedures for Hydration of Various Nitriles
General procedure: To a 25 mL round-bottom flask equipped with magnetic stirrer were added nitrile (2 mmol), acetaldoxime (6 mmol), sodium molybdate (VI) dihydrate (0.2 mmol) and H2O (10 mL). The mixture was heated to reflux for 5-16 h. After cooling to room temperature, the solution was directly evaporated to dryness and the residue was purified by column chromatography on silica gel (ethylacetate/n-hexane) to give the corresponding amide. |
| 91% |
With C14H30ClN3PRh; lithium hydroxide monohydrate at 100℃; for 24h; Inert atmosphere; Schlenk technique; |
|
| 91% |
With lithium hydroxide monohydrate at 130℃; for 1h; Microwave irradiation; |
|
| 91% |
With potassium hydroxide In lithium hydroxide monohydrate at 60℃; for 3h; Green chemistry; |
2.4 General procedure for hydration of nitrileto amide compounds
General procedure: In a 50 mL round-bottomed flask nitriles (1.0 mmol),catalyst (25 mg, 0.05 mol% Fe), KOH (1 mmol) andwater (5 mL) were mixed and allowed to react for therequired amount of time at temperature 60 °C withconstant stirring. The progress of the reaction wasmonitored with thin layer chromatography (TLC).After completion of the reaction, the catalyst wasremoved from the reaction mixture by simple filtration.The resulting mixture was extracted from the filtrate by using water and ethyl acetate. The combinedextract was dried over anhydrous Na2SO4. Afterevaporation of the solvent under reduced pressureusing a rotary evaporator, the residue was purified bycolumn chromatography (silica gel, ethyl acetate:hexane 1:1) as eluent to get the desired products. Forrecycling experiments, the catalyst was washed severaltimes after each cycle with water and diethyl ether.After overnight drying at 110 °C, the recovered catalystwas subjected to successive runs under identicalreaction conditions. |
| 91% |
With cis-[Mn(2,6-bis(di-tert-butylphosphinomethyl)pyridine)(CO)2]; lithium hydroxide monohydrate In <i>tert</i>-butyl alcohol at 90℃; for 24h; Green chemistry; |
|
| 90% |
Stage #1: 4-chlorobenzonitrile With Cs2CO3 In pyrrolidin-2-one at 130℃; for 2h; Sealed vessel;
Stage #2: With methanol In pyrrolidin-2-one; dichloromethane at 20℃; Filtering through Celite pad; |
General procedure for hydration of (hetero)aryl nitriles 1
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. |
| 90% |
With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 80℃; for 2.5h; |
|
| 90% |
With potassium pyrosulfate; potassium aquapentachlororuthenate(III); potassium hydroxide at 100℃; for 0.5h; Sonication; |
|
| 90% |
With lithium hydroxide monohydrate; sodium hydroxide In ethanol at 90℃; for 17h; |
|
| 90% |
With acetamide; Pd3P0.95 In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 4h; |
|
| 89% |
With 4Cu(1+)*4H2O*4I(1-); lithium hydroxide monohydrate at 100℃; for 21h; |
|
| 88% |
With dopamine-functionalized magnetic nanoferrite-supported ruthenium hydroxide In lithium hydroxide monohydrate at 130℃; for 0.5h; Microwave irradiation; |
|
| 88% |
Stage #1: 4-chlorobenzonitrile With Br(1-)*C24H30N4Rh(1+); lithium hydroxide monohydrate In isopropanol at 25℃; for 0.5h; Inert atmosphere;
Stage #2: With potassium-t-butoxide In isopropanol at 25℃; for 6h; Inert atmosphere; |
|
| 88% |
With nanoferrite-[Ru(OH)x] In lithium hydroxide monohydrate at 130℃; for 0.5h; Sealed tube; Microwave irradiation; |
|
| 88% |
With CoCl2·6H2O; oxygen; Ethane-1,2-diamine; zinc In neat (no solvent) at 120℃; for 12h; Autoclave; |
Typical procedure for the preparation of benzamide from phenylcyanidein the presence of oxygen
General procedure: The reaction was carried out in a 100-mL stainless steel autoclave. Phenylcyanide (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl26H2O (0.24 g, 1.00 mmol) and Zn (0.07 g, 1.00 mmol) and the vessel was placed in an autoclave. For some of the reactions that were carried out in solvent, 5 mL of solvent was also added. The autoclave was pressurized to 5.00 atm with O2. The mixture was stirred in a preheated oil bath at 120 C for 12 h. Then, the reaction mixture was cooled to room temperature and the product was purified by column chromatography on silica gel using n-hexane:CH2Cl2 (1:1) to give the benzamide(88 % yield). |
| 88% |
With potassium hydroxide In isopropanol at 40℃; for 5h; |
|
| 87% |
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; lithium hydroxide monohydrate at 100℃; for 0.25h; Inert atmosphere; Sealed tube; |
|
| 85% |
With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide for 0.0833333h; Ambient temperature; |
|
| 84% |
With C20H24ClNO2Ru; sodium hydroxide In isopropanol at 79.84℃; for 4h; Inert atmosphere; Schlenk technique; |
2.3 General procedure for the nitrile hydration with half-sandwich ruthenium catalysts
General procedure: To a stirred solution of half-sandwich ruthenium complex (0.25mol%) in 2.0mL of isopropanol were added NaOH (0.3mmol) and benzonitrile (0.3mmol) followed by stirring for 4h at 353K. After completion of the reaction (monitored by TLC), the resulting solution was evaporated to dryness at reduced pressure. The crude products loaded directly onto a column of silica gel and purified by column chromatography to yield the corresponding amides [15]. |
| 84% |
With water extract of pomelo, peel at 150℃; for 0.5h; Sealed tube; Green chemistry; |
3.3. General Procedure for the Hydrolysis of Nitriles in WEPPA (Taking 1a as an Example
General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield. |
| 83% |
With lithium hydroxide monohydrate at 130℃; for 1h; Microwave irradiation; |
|
| 83% |
With RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}; lithium hydroxide monohydrate at 40℃; for 9.5h; Sealed tube; Inert atmosphere; |
|
| 82% |
With acetamide; C36H38Cl6N6Pd3S2 In tetrahydrofuran; lithium hydroxide monohydrate at 80℃; for 5h; |
|
| 80% |
With [RuCl2-{κ(1)(P)-Ph2P(3-NHt-BuCH2C6H4)}(η(6)-1,3,5-C6H3Me3)]; lithium hydroxide monohydrate at 100℃; for 24h; Inert atmosphere; Sealed tube; |
|
| 80% |
With sulfuric acid; kaolin; lithium hydroxide monohydrate for 24h; Reflux; chemoselective reaction; |
|
| 80% |
With Acetaldehyde oxime; Cp*Rh(H2O)3(OTf)2 In lithium hydroxide monohydrate at 50℃; for 6h; Schlenk technique; |
6 Example 6: 4-Chlorobenzamide
A solution of 4-chlorobenzonitrile (138 mg, 1 mmol), [Cp * Rh (H2O)3] [OTf]2(3.0 mg, 0.005 mmol, 0.5 mol%), acetaldehyde oxime (65 mg, 1.1 mmol) and water (1 ml) were successively added to a 25 ml Schlenk reaction flask.The reaction mixture was reacted at 50 ° C for 6 hours, then cooled to room temperature, and the water was removed by rotary evaporation to remove the title product. The yield was 80% |
| 79% |
With RuCl2(η6-C6Me6)(1-benzyl-3,5-diaza-1-azonia-7-phosphaadamantane chloride); lithium hydroxide monohydrate at 100℃; for 1h; Inert atmosphere; Neutral aq. solution; chemoselective reaction; |
|
| 79% |
With [Ru(OTf){η6:κ1(P)-PPh2-binaphthyl}{PPh2(OH)}][OTf] In lithium hydroxide monohydrate at 100℃; for 5h; Inert atmosphere; Sealed tube; |
|
| 78% |
With sodium perborate; lithium hydroxide monohydrate In methanol at 50℃; for 1h; |
|
| 78% |
With tetrakis(pyridine)cobalt(II) dichromate In N,N-dimethyl-formamide at 90℃; for 3h; |
|
| 78% |
With caesium hydroxide; lithium hydroxide monohydrate; dimethyl sulfoxide at 60℃; for 36h; Schlenk technique; Green chemistry; |
|
| 74% |
With OsCl2(η6-p-cymene)(PMe2OH); lithium hydroxide monohydrate at 80℃; for 1h; Inert atmosphere; Sealed tube; |
|
| 73% |
With potassium peroxomonosulfate; propan-2-one In lithium hydroxide monohydrate at 5 - 20℃; for 8.5h; pH=7.5; |
|
| 72% |
With lithium hydroxide monohydrate for 7h; Heating; |
|
| 71% |
With lithium hydroxide monohydrate at 120℃; for 17h; Green chemistry; |
2.4 Typical procedure for the Ni NPs/HT catalyzed hydration of nitriles to amides
General procedure: Ni NPs/HT (0.05 g) is placed in a heavy-walled pressure tube, followed by the addition of water (4 ml) and benzonitrile (1 mmol), and the reaction mixture is vigorously stirred at 120 °C in an oil bath for the specified time in tables. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture is extracted with ethyl acetate, after the extraction, the catalyst is removed by filtration, and the filtrate is cooled to 0 °C, and white crystals are precipitated from the filtrate. The crystalline product was obtained by simple filtration and dried in vacuo at room temperature to give analytically amide product. In cases where the product not precipitated out, the reaction mixture was extracted with ethyl acetate, subsequent purification by column chromatography on silica gel provided amide product. |
| 70% |
With ammonium hydroxide; caesium hydroxide monohydrate at 100℃; for 12h; Schlenk technique; Sealed tube; |
|
| 64% |
With hydroxyamino hydrochloride; sodium hydroxide In ethanol; lithium hydroxide monohydrate for 6h; Reflux; |
|
| 62% |
With sodium perborate In 1,4-dioxane; lithium hydroxide monohydrate at 89℃; for 1.5h; |
|
| 56% |
With copper oxide (I); ammonium hydroxide; oxygen In dimethyl sulfoxide at 100℃; Sealed tube; |
4 Synthesis Example 4 Synthesis of 4-chlorobenzamide
50 mol% Cu2O was added to the reaction vessel, the reaction tube was evacuated and filled with oxygen. 0.2 mmol of 4-chlorobenzonitrile, 0.7 mmol of ammonia water and 2 ml of dimethylsulfoxide were added in an oxygen atmosphere. The reaction vessel was sealed and reacted at 100 ° C ,After the reaction was completed, it was washed with water, extracted with ethyl acetate, dried and concentrated under reduced pressure to remove the solvent. The crude product was separated by column chromatography to give the desired product in a yield of 56%. |
| 55% |
With acetamide; anhydrous zinc chloride In tetrahydrofuran; lithium hydroxide monohydrate for 0.00972222h; microwave irradiation; |
|
|
With potassium hydroxide; dihydrogen peroxide |
|
|
With hydrogenchloride |
|
|
With sodium hydroxide; dihydrogen peroxide; dimethyl sulfoxide In methanol; lithium hydroxide monohydrate at 50℃; for 1h; |
|
|
With urea-hydrogen peroxide; potassium carbonate In lithium hydroxide monohydrate; propan-2-one for 0.75h; Ambient temperature; |
|
|
With sodium hydroxide; dihydrogen peroxide; dimethyl sulfoxide In methanol; lithium hydroxide monohydrate at 50℃; for 1h; |
|
|
With lithium hydroxide monohydrate at 139.85℃; for 6h; |
|
|
With lithium hydroxide monohydrate for 6h; |
|
|
With nitrile hydratase from Rhodopseudomonas palustris CGA009 In methanol at 30℃; for 17h; aq. phosphate buffer; chemoselective reaction; |
|
|
With lithium hydroxide monohydrate at 149.84℃; for 6h; |
|
| 97 %Chromat. |
With ammonia; lithium hydroxide monohydrate In 1,4-dioxane at 130℃; for 3h; Autoclave; Inert atmosphere; |
|
| 95 %Chromat. |
With lithium hydroxide monohydrate; palladium diacetate In N,N-dimethyl-formamide at 89.84℃; for 12h; |
|
| 95 %Chromat. |
With lithium hydroxide monohydrate at 160℃; for 40h; |
|
| 99 %Chromat. |
With lithium hydroxide monohydrate at 60℃; for 3h; chemoselective reaction; |
|
| 95 %Chromat. |
With [Os(η6-p-cymene)(OH)(1,3-bis(2,6-diisopropylphenyl)imidazolylidene)](CF3SO3); lithium hydroxide monohydrate; isopropanol; potassium hydroxide In para-xylene at 120℃; for 3h; Schlenk technique; Inert atmosphere; |
|
|
With RuCl2(pyrazole)(DMSO)4; lithium hydroxide monohydrate at 80℃; for 20h; Sealed tube; |
|
| > 99 %Chromat. |
With lithium hydroxide monohydrate at 150℃; for 6h; |
3.5. A Typical Procedure for the Hydration of Nitriles
General procedure: Ag/Fe3O4 catalyst (3.0 mol %), water (3.0 mL), and the corresponding nitrile (1.0 mmol) were introduced into a stainless steel reactor. After the reaction, the catalysts were separated from the solution by external magnet. The reaction products were analyzed by mass spectra on GC-MS. (Figures S1-S10). |
|
With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; valeraldehyde oxime In toluene at 100℃; for 6h; Inert atmosphere; Schlenk technique; |
|
| 95 %Chromat. |
With [Ru(CO)(pyridoxal-4-methyl-thiosemicarbazide hydrochloride)(triphenylphosphine)2] In methanol; lithium hydroxide monohydrate at 80℃; for 1h; |
2.5. General procedure for the hydration of nitriles to amides
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 mol%) 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 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; lithium hydroxide monohydrate In tetrahydrofuran at 130℃; for 12h; |
|
|
With C40H45ClN3O2PRu In methanol; lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere; Schlenk technique; Green chemistry; |
4.7. General procedure for the hydration of nitriles to amides
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 mol%) 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. |
| 90 %Chromat. |
With poly(amic acid) salt-stabilized silver nanoparticles; air In lithium hydroxide monohydrate at 90℃; for 10h; |
|
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