2-Pyridinemethanol (Piconol) [C6H7NO] by Asch

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69 reactions in Reaxys

2018-04-04 15h:00m:24s (UTC)

N OH

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Search as: As drawn AND (IDE.XRN=107849)

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Rx-ID: 1523911 View in Reaxys 1/69 Yield 100 %

Conditions & References With 1-Benzyl-3,5-bis(1-pyrrolidinylcarbonyl)-1,4-dihydropyridine, zinc(II) perchlorate, anionic SDS micelle in water, T= 50 °C , different Zn(ClO4)2*6H2O concentration, in the presence and without of SDS, Rate constant Awano, Hiroshi; Tagaki, Waichiro; Journal of the Chemical Society, Chemical Communications; nb. 14; (1985); p. 994 - 996 View in Reaxys

100 %

With magnesium(II) perchlorate, polymer-bound NADH (2a) in acetonitrile, benzene, Time= 120h, T= 80 °C , Further byproducts given Dupas, G.; Bourguignon, J.; Ruffin, C.; Queguiner, G.; Tetrahedron Letters; vol. 23; nb. 49; (1982); p. 5141 - 5144 View in Reaxys

100 %

With 1-Benzyl-3,5-bis(1-pyrrolidinylcarbonyl)-1,4-dihydropyridine, zinc(II) perchlorate, anionic SDS (C12H25OSO3Na) micelle in water, T= 50 °C Awano, Hiroshi; Tagaki, Waichiro; Journal of the Chemical Society, Chemical Communications; nb. 14; (1985); p. 994 - 996 View in Reaxys

99 %

With hydrogen in ethanol, water, Time= 0.00611111h, T= 40 °C , p= 22502.3Torr , Flow reactor, Green chemistry, chemoselective reaction Osako, Takao; Torii, Kaoru; Hirata, Shuichi; Uozumi, Yasuhiro; ACS Catalysis; vol. 7; nb. 10; (2017); p. 7371 - 7377 View in Reaxys

98 %

With subst. dihydroquinoline, zinc(II) chloride, Time= 15h, T= 50 °C , pH 4.7; in the dark Tabushi, Iwao; Kuroda, Yasuhisa; Mizutani, Tadashi; Journal of the American Chemical Society; vol. 106; nb. 11; (1984); p. 3377 - 3378 View in Reaxys

98 %

With diisopropoxyaluminium trifluoroacetate in dichloromethane, Time= 1h, Ambient temperature Akamanchi; Varalakshmy; Chaudhari; Synlett; vol. 1997; nb. 4; (1997); p. 371 - 372 View in Reaxys

94 %

Stage 1: With tetrabutylammonium tricarbonylnitrosylferrate, tricyclohexylphosphine in 1,4-dioxane, T= 50 °C , Inert atmosphere Stage 2: With water, sodium hydroxide in 1,4-dioxane, methanol, Time= 1.5h, T= 20 °C , Inert atmosphere, chemoselective reaction Dieskau, Andre P.; Begouin, Jeanne-Marie; Plietker, Bernd; European Journal of Organic Chemistry; nb. 27; (2011); p. 5291 - 5296 View in Reaxys

92 %

Stage 1: With C39H46ClCuN2, phenylsilane, potassium tert-butylate in tetrahydrofuran, Time= 0.333333h, T= 20 °C , Schlenk technique, Inert atmosphere, Glovebox Stage 2: With water, sodium hydroxide in tetrahydrofuran, methanol, Time= 1h, Schlenk technique, Glovebox, chemoselective reaction Roy, Sudipta Raha; Sau, Samaresh Chandra; Mandal, Swadhin K.; Journal of Organic Chemistry; vol. 79; nb. 19; (2014); p. 9150 - 9160 View in Reaxys

85 %

Typical procedure and Spectral Data for Products General procedure: An oven-dried pressure tube containing a Teflon-coated stirring bar was charged with Pd(OAc)2 (11.2 mg, 5 molpercent), PCy3 (21 mg, 7.5 molpercent) and aldehyde(1 mmol).The tube was sealed, evacuated and backfilled with N2. 1 mL of dioxane was subsequently injected. After the mixture was stirred at room temperature for 15 min, H2O (180 mg, 10 equiv) and HCO2H (184 mg, 4 equiv) were injected and the reaction was heated to 90 oC for 18 h. After the reaction was completed,

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the solvent was removed under vacuo. The residues were purified by flash column chromatography on silica gel to afford 87 mg of benzyl alcohol in 81 percent yield. With formic acid, water, palladium diacetate, tricyclohexylphosphine in 1,4-dioxane, Time= 18h, T= 90 °C , Inert atmosphere, Sealed tube, chemoselective reaction Wang, Anwei; Yang, Zhiyong; Liu, Jidan; Gui, Qingwen; Chen, Xiang; Tan, Ze; Shi, Ji-Cheng; Synthetic Communications; vol. 44; nb. 2; (2014); p. 280 - 288 View in Reaxys 83 %

Stage 1: With diphenylsilane, caesium carbonate, Time= 2h, T= 20 °C , Schlenk technique Stage 2: With sodium hydroxide in methanol, water, T= 70 °C , Schlenk technique, chemoselective reaction Zhao, Mengdi; Xie, Weilong; Cui, Chunming; Chemistry - A European Journal; vol. 20; nb. 30; (2014); p. 9259 - 9262 View in Reaxys

78 %

With potassium hydroxide, nickel-incorporated hexagonal mesoporous aluminophosphate in isopropyl alcohol, Time= 3h, T= 82.84 °C Selvam, Parasuraman; Mohapatra, Susanta K.; Sonavane, Sachin U.; Jayaram, Radha V.; Tetrahedron Letters; vol. 45; nb. 9; (2004); p. 2003 - 2007 View in Reaxys

75.3 %

With isopropyl alcohol, potassium hydoxide, Time= 12h, T= 69.84 °C , Green chemistry Patra, Astam K.; Kundu, Sudipta K.; Kim, Dukjoon; Bhaumik, Asim; ChemCatChem; vol. 7; nb. 5; (2015); p. 791 - 798 View in Reaxys

72 %

With Decaborane in tetrahydrofuran, water, Time= 1h, T= 20 °C Lee, Seung Hwan; Nam, Mi Hye; Cho, Min Young; Yoo, Byung Woo; Rhee, Hak June; Yoon, Cheol Min; Synthetic Communications; vol. 36; nb. 17; (2006); p. 2469 - 2474 View in Reaxys

61 %

With (7,8-benzoquinolinato)hydrido(aqua)bis(triphenylphosphine)iridium(III) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, hydrogen, N-ethyl-N,N-diisopropylamine in toluene, Time= 4h, T= 80 °C , p= 760.051Torr Manas, Michael G.; Graeupner, Jonathan; Allen, Laura J.; Dobereiner, Graham E.; Rippy, Kerry C.; Hazari, Nilay; Crabtree, Robert H.; Organometallics; vol. 32; nb. 16; (2013); p. 4501 - 4506 View in Reaxys

60 %

1 : Synthesis of 2-hydroxymethylpyridine The raw material (F) 2-pyridinecarboxaldehyde is distilled under reduced pressure before use,Purified ones were used within 15 minutes.A rotor was put in a 200 mL reaction vessel and dry THF (90 mL),2-pyridinecarboxaldehyde (1.6 g, 14.6 mmol) was added to a mixed solvent of distilled water (10 mL) and stirred.After sufficiently cooling the reaction vessel with an ice bath,NaBH 4 (1.2 g 31.7 mmol) was added.After stirring at room temperature for 90 minutes,4 M HCl was added while cooling with an ice bath,NaBH 4 was completely dissolved.It was confirmed that the pH dropped to 2 by pH test paper.After THF was concentrated with an evaporator in the presence of an alkali trap, 50 mL of CHCl 3 was added thereto, and Na 2 CO 3 was added little by little to neutralize while cooling with an ice bath. Appropriate amounts of H 2 O and CHCl 3 were added and extracted with CHCl 3 (50 mL × 4) using a separating funnel.Na 2 SO 4 was added and the mixture was dehydrated and then concentrated to obtain 1.0 g of a colorless oil.Yield: 60percent (1.0 g) With sodium tetrahydroborate, water in tetrahydrofuran, Time= 1.5h, T= 20 °C , Cooling with ice Patent; THE DOSHISHA; KODERA, MASAHITO; ZAOPUTRA, ANTONIUS ANDRE; TSUJI, TOMOKAZU; (15 pag.); JP2017/57177; (2017); (A) Japanese View in Reaxys

51 %

2.5. Catalysis: general procedure for the transfer hydrogenationreactions General procedure: A mixture of ketone (1 mmol), a known mole percent of the catalystand KOH (0.06 mmol) was dissolved in 2-propanol (5 mL), and the mixture was heated under reflux for the desired period oftime. The catalyst was removed as precipitate from the reactionmixture by the addition of diethyl ether followed by filtrationand subsequent neutralization with 5 mL of 1 M HCl. Then theether layer was passed through a short path of silica gel and the filtratewas subjected to GC analysis for identification andquantification.

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With C51H46N3OP2Ru, potassium hydoxide in isopropyl alcohol, Time= 2h, T= 80 °C Chowdhury, Nabanita Saha; Guharoy, Chhandasi; Butcher, Ray J.; Bhattacharya, Samaresh; Inorganica Chimica Acta; vol. 406; (2013); p. 20 - 26 View in Reaxys 50 %

With sodium tetrahydroborate in methanol, 1) 0 deg C, 0.5 h, 2) reflux, 1 h Leitis, L. Ya.; Shimanskaya, M. V.; J. Appl. Chem. USSR (Engl. Transl.); vol. 53; nb. 4; (1980); p. 917 - 920,724 - 727 View in Reaxys

30 %

Stage 1: With (dppe)2Fe(H)2*(C7H8)2, Na-tetrakis(ethoxy)borate in toluene, Time= 3h, T= 100 °C , visible light irradiation, Inert atmosphere Stage 2: With water, sodium hydroxide in methanol, toluene, Time= 16h, T= 20 °C Castro, Luis C. Misal; Bezier, David; Sortais, Jean-Baptiste; Darcel, Christophe; Advanced Synthesis and Catalysis; vol. 353; nb. 8; (2011); p. 1279 - 1284 View in Reaxys

16 %

General procedure for the hydrogenation reaction General procedure: In a glovebox, aldehydes (0.25 mmol) and the Hantzsch ester 1 (95 mg, 0.38 mmol) were added to asolution of tris[3,5-bis(trifluoromethy)phenyl]borane (9) (8.1 mg, 12.5 μmol) in 1 mL of anhydrous1,4-dioxane. The reaction mixture was stirred at 25 or 100 C for 12 h. An internal standard (biphenylor mesitylene) was added to the reaction mixture and filtrated through a cotton plug. The resultingsolution was analyzed with gas chromatography. With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, tris[3,5-bis(trifluoromethyl)phenyl]-borane in 1,4-dioxane, Time= 12h, T= 100 °C , Glovebox Hamasaka, Go; Tsuji, Hiroaki; Uozumi, Yasuhiro; Synlett; vol. 26; nb. 14; (2015); p. 2037 - 2041; Art.No: ST-2015-B0414-L View in Reaxys With magnesium(II) perchlorate, 1-Benzyl-1,4-dihydronicotinamide in acetonitrile, T= 80 °C , Yield given Tintillier, P.; Dupas, G.; Bourguignon, J.; Queguiner, G.; Tetrahedron Letters; vol. 27; nb. 21; (1986); p. 2357 - 2360 View in Reaxys With 4-aza-N-benzyl-bicyclolt;2,2,2gt;octyl ammonium borohydride in tert-butyl alcohol, Time= 0.23h, Yield given Firouzabadi; Afsharifar; Synthetic Communications; vol. 22; nb. 4; (1992); p. 497 - 507 View in Reaxys With sodium methylate in methanol, Time= 3h, Ambient temperature, Yield given Kinoshita; Ohishi; Journal of Heterocyclic Chemistry; vol. 31; nb. 6; (1994); p. 1599 - 1603 View in Reaxys With barium dihydroxide, formaldehyd, Time= 0.333333h, T= 100 - 110 °C Varma, Rajender S.; Naicker, Kannan P.; Liesen, Per J.; Tetrahedron Letters; vol. 39; nb. 46; (1998); p. 8437 - 8440 View in Reaxys With potassium hydroxide, isopropyl alcohol, Fe(III) substituted hexagonal mesoporous aluminophosphate, Time= 6h, T= 82.85 °C Sonavane, Sachin U.; Mohapatra, Susanta K.; Jayaram, Radha V.; Selvam, Parasuraman; Chemistry Letters; vol. 32; nb. 2; (2003); p. 142 - 143 View in Reaxys

63 % Chromat.

With potassium hydroxide, isopropyl alcohol, molecular sieve, Time= 4h, T= 82.84 °C Mohapatra, Susanta K.; Sonavane, Sachin U.; Jayaram, Radha V.; Selvam, Parasuraman; Organic Letters; vol. 4; nb. 24; (2002); p. 4297 - 4300 View in Reaxys With Ru(P,O,P-xantphos)(S-dmso)Cl2, isopropyl alcohol, potassium hydoxide, Time= 10h, Reflux

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Kharat, Ali Nemati; Bakhoda, Abolghasem; Jahromi, Bahareh Tamaddoni; Inorganic Chemistry Communications; vol. 14; nb. 7; (2011); p. 1161 - 1164 View in Reaxys With 1-Benzyl-1,4-dihydronicotinamide, chloro(η3-S,S,N)-[2,6-bis(3-isopropylimidazol-2-thione-1-yl)]pyridinezinc(II) aquatrichlorozincate in chloroform-d1, Time= 20h, Reflux Miecznikowski, John R.; Lo, Wayne; Lynn, Matthew A.; O'Loughlin, Brianne E.; Dimarzio, Amanda P.; Martinez, Anthony M.; Lampe, Lorraine; Foley, Kathleen M.; Keilich, Lauren C.; Lisi, George P.; Kwiecien, Daniel J.; Pires, Cristina M.; Kelly, William J.; Kloczko, Nathan F.; Morio, Kaitlyn N.; Inorganica Chimica Acta; vol. 376; nb. 1; (2011); p. 515 - 524 View in Reaxys With rat brain voltage-dependent potassium channel Kvη2-subunit-bound NADPH in ethanol, T= 22 °C , pH= 7.5, aq. phosphate buffer, Enzymatic reaction, Kinetics Alka, Kumari; Ryan, Barry J.; Dolly, J. Oliver; Henehan, Gary T.M.; International Journal of Biochemistry and Cell Biology; vol. 42; nb. 12; (2010); p. 2012 - 2018 View in Reaxys With glucose dehydrogenase, D-glucose, (R)-specific alcohol dehydrogenase from Candida maris IFO10003, NADH in dimethyl sulfoxide, Time= 17h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction Kawano, Shigeru; Yano, Miho; Hasegawa, Junzo; Yasohara, Yoshihiko; Bioscience, Biotechnology and Biochemistry; vol. 75; nb. 6; (2011); p. 1055 - 1060 View in Reaxys Stage 1: With (.eta.5-C5H5)Fe(CO)2(triphenylphosphino) hexafluorophosphate in tetrahydrofuran, Time= 24h, T= 30 °C , Irradiation Stage 2: With methanol, sodium hydroxide in water, Time= 1h, T= 20 °C , chemoselective reaction Zheng, Jianxia; Misal Castro, Luis C.; Roisnel, Thierry; Darcel, Christophe; Sortais, Jean-Baptiste; Inorganica Chimica Acta; vol. 380; nb. 1; (2012); p. 301 - 307 View in Reaxys With 1-Benzyl-1,4-dihydronicotinamide, 2C19H27ClN7S2Zn(1+)*Cl6Zn2 (2-) in chloroform-d1, Time= 20h, Reflux, Inert atmosphere Miecznikowski, John R.; Lo, Wayne; Lynn, Matthew A.; Jain, Swapan; Keilich, Lauren C.; Kloczko, Nathan F.; O'Loughlin, Brianne E.; Dimarzio, Amanda P.; Foley, Kathleen M.; Lisi, George P.; Kwiecien, Daniel J.; Butrick, Elizabeth E.; Powers, Erin; Al-Abbasee, Raed; Inorganica Chimica Acta; vol. 387; (2012); p. 25 - 36 View in Reaxys 2.3. Reactivity General procedure: In a typical reaction, 0.1 mmol of an electron-poor aldehyde (4-nitrobenzaldehyde or pyridine 2-carboxaldehyde), 0.2 mmol of BNAH, and 0.1 mmol of the zinc complex or 0.1 mmol ZnCl2 were dissolved in 3 mL of CDCl3. The reaction was heated at reflux. Aliquots of the reaction were taken at certain times and analyzed using 1H NMR spectroscopy. All data are averages of at least two runs. With 1-Benzyl-1,4-dihydronicotinamide, C17H23Cl2N7S2Zn in chloroform-d1, Time= 20h, Reflux, Catalytic behavior, Reagent/ catalyst Miecznikowski, John R.; Jasinski, Jerry P.; Lynn, Matthew A.; Jain, Swapan S.; Butrick, Elizabeth E.; Drozdoski, Anne Elise R.; Archer, Kerry A.; Panarra, Jason T.; Inorganica Chimica Acta; vol. 394; (2013); p. 310 - 321 View in Reaxys < 1 %Chromat.

2. Experimental General procedure: Fe(BF4)2·6H2O (0.7 mg; 0.002 mmol) and tris[2-(diphenyl-phosphino)-ethyl]phosphine [P(CH2CH2PPh2)3; tetraphos] (1.4 mg; 0.002 mmol) are placed in a Schlenk-tube under argon atmosphere. 1 mL dry tetrahydrofurane is added and the purple solution is stirred for 2 min. Cinnamaldehyde (63 μL; 0.5 mmol) and 100 μL n-hexadecane as an internal GC-standard are injected and a sample is taken for GC-analysis. The solution is heated to 60 °C and the reaction starts by addition of 1.1 equiv formic acid (22 μL; 0.55 mmol). After 2 h, a second sample is taken for GC-analysis and conversion and yield are determined by comparison with authentic samples. For the isolation, the reaction is scaled up by a factor of 20. When the reaction is completed, the reaction solution is diluted with a mixture of n-hexane and ethyl acetate (3:1), filtered through a plug of silica and the solvent removed in vacuum.

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With formic acid, iron(II) tetrafluoroborate hexahydrate, tris(2-diphenylphosphinoethyl)phosphine in tetrahydrofuran, Time= 2h, T= 60 °C , Schlenk technique, Inert atmosphere Wienhoefer, Gerrit; Westerhaus, Felix A.; Junge, Kathrin; Beller, Matthias; Journal of Organometallic Chemistry; vol. 744; (2013); p. 156 - 159 View in Reaxys 97 %Spectr. Stage 1: With Cp(CO)2Mn(IMes), diphenylsilane in toluene, Time= 1h, T= 25 °C , Schlenk technique, Inert atmosphere, UVirradiation Stage 2: With sodium hydroxide in methanol, toluene, Time= 2h, T= 20 °C , Schlenk technique, Inert atmosphere Zheng, Jianxia; Elangovan, Saravanakumar; Valyaev, Dmitry A.; Brousses, Remy; Cesar, Vincent; Sortais, Jean-Baptiste; Darcel, Christophe; Lugan, Noel; Lavigne, Guy; Advanced Synthesis and Catalysis; vol. 356; nb. 5; (2014); p. 1093 1097 View in Reaxys With sodium tetrahydroborate, water in acetonitrile Pratihar, Sanjay; Organic and Biomolecular Chemistry; vol. 12; nb. 30; (2014); p. 5781 - 5788 View in Reaxys 41 %Chromat.

Reduction of benzaldehyde to benzylalcohol General procedure: Knölker iron complex 2a (3 mol percent,12.6 mg), paraformaldehyde (300 mg, 10 mmol), and Na2CO3 (106 mg, 1 mmol,1.0 equiv) and a stirring bar were charged in a pressure tube and flushed withargon. DMSO (1.0 mL), degassed water (1.0 mL), and benzaldehyde (1 mmol)were added under an argon atmosphere to the pressure tube with a syringe.The pressure tube was placed in oil and heated at 120 C for 24 h, then cooledto room temperature. The reaction mixture was neutralized with HCl (1M) andstirred for 30 min. After extraction with EtOAc for 3 times, the combinedorganic layers were dried over MgSO4. The crude product was purified bycolumn chromatography (Heptane/EtOAc: 70:30). The reaction was cooled toroom temperature and hexadecane (100 lL) was added as a GC internalstandard. With formaldehyd, tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron, water, sodium carbonate in dimethyl sulfoxide, Time= 24h, T= 120 °C , Inert atmosphere, Sealed tube Natte, Kishore; Li, Wanfang; Zhou, Shaolin; Neumann, Helfried; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; nb. 9; (2015); p. 1118 - 1121 View in Reaxys With potassium tert-butylate, hydrogen in ethanol, Time= 0.166667h, T= 25 °C , p= 3750.38Torr Gorgas, Nikolaus; Stöger, Berthold; Veiros, Luis F.; Pittenauer, Ernst; Allmaier, Günter; Kirchner, Karl; Organometallics; vol. 33; nb. 23; (2014); p. 6905 - 6914 View in Reaxys With sodium tetrahydroborate in methanol, Time= 2h Huang, Guoli; Feng, Li; Liu, Bo; He, Yi; Li, Yiming; Chen, Yegao; Natural Product Research; vol. 29; nb. 17; (2015); p. 1650 - 1656 View in Reaxys

95 %Chromat.

2.2 Typical Procedures for Transfer Hydrogenationof Carbonyl Compounds General procedure: The transfer hydrogenation reactions were carried out under argon atmosphere using standard Schlenk technique unless otherwise stated. Benzyl aldehyde (1 mmol), formic acid (3.5 eqiv.), and water (3.5 mL) were injected into a sealed tube with the catalyst (0.048 g Ir(at)CN) and sodium hydroxide (2 eqiv.) under Ar. Then the mixture was stirred under 100 °C (with an oil bath) for the given time. After cooled, the reaction mixture was diluted with 3 9 5 mL of ether, and then the catalyst Ir(at)CN was filtered. The conversions and yields were determined by GC using n-hexadecane as an internal standard. With formic acid, sodium hydroxide in water, Time= 18h, T= 100 °C , Inert atmosphere, Schlenk technique, Sealed tube, chemoselective reaction Wang, Zhi; Huang, Lei; Geng, Longfei; Chen, Rizhi; Xing, Weihong; Wang, Yong; Huang, Jun; Catalysis Letters; vol. 145; nb. 4; (2015); p. 1008 - 1013; Art.No: 1473 View in Reaxys Reaction Steps: 2 1: C43H48FeN2 / neat (no solvent) / 0.5 h / 70 °C / Glovebox; Schlenk technique

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2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C With C43H48FeN2, tetrabutyl ammonium fluoride in tetrahydrofuran Wekesa, Francis S.; Arias-Ugarte, Renzo; Kong, Lydia; Sumner, Zachary; McGovern, Gregory P.; Findlater, Michael; Organometallics; vol. 34; nb. 20; (2015); p. 5051 - 5056 View in Reaxys 97 %Spectr. With [Fe(PNPMe-iPr)(CO)(H)(Br)], hydrogen, 1,8-diazabicyclo[5.4.0]undec-7-ene in ethanol, Time= 16h, T= 40 °C , p= 22502.3Torr , chemoselective reaction Gorgas, Nikolaus; Stöger, Berthold; Veiros, Luis F.; Kirchner, Karl; ACS Catalysis; vol. 6; nb. 4; (2016); p. 2664 - 2672 View in Reaxys 2.3. Reactivity with synthetic model zinc complexes Model zinc complex 3c was synthesized in our laboratoryaccording to previously published protocols [6,23,25]. In a typicalreaction, 0.1 mmol of an aldehyde substrate, 0.2 mmol of BNAH,and 0.1 mmol of the zinc complex or 0.1 mmol ZnCl2 were dissolvedin 3 mL of CDCl3. The reaction was heated at reflux. Aliquotsof the reaction were taken at certain times and analyzed using 1HNMR spectroscopy. All data are averages of at least two runs. All ofthe reagents and solvents were purchased from Acros Organicsexcept for 2-pyridine carboxaldehyde, which was purchased fromAlfa Aesar. With C19H27ClN7S2Zn(1+), N-benzyl-1,4-dihydronicotinamide in chloroform-d1, Time= 20h, Reflux, Reagent/catalyst Sunderland, James R.; Tao, Xingjian; Butrick, Elizabeth E.; Keilich, Lauren C.; Villa, Christine E.; Miecznikowski, John R.; Jain, Swapan S.; Polyhedron; vol. 114; (2016); p. 145 - 151 View in Reaxys With sodium tetrahydroborate, Inert atmosphere Ogiwara, Yohei; Ono, Yuji; Sakai, Norio; Synthesis (Germany); vol. 48; nb. 23; (2016); p. 4143 - 4148; Art.No: SS-2016F0462-OP View in Reaxys Reaction Steps: 2 1: C18H37F5FeP4 / tetrahydrofuran / 40 °C / Schlenk technique; Inert atmosphere 2: sodium hydroxide / methanol; water / 24 h / 60 °C / Schlenk technique; Inert atmosphere With C18H37F5FeP4, sodium hydroxide in tetrahydrofuran, methanol, water Zheng, Tingting; Li, Junye; Zhang, Shumiao; Xue, Benjing; Sun, Hongjian; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter; Organometallics; vol. 35; nb. 20; (2016); p. 3538 - 3545 View in Reaxys With sodium tetrahydroborate in methanol Galletti, Paola; Pori, Matteo; Funiciello, Federica; Soldati, Roberto; Ballardini, Alberto; Giacomini, Daria; ChemSusChem; vol. 7; nb. 9; (2014); p. 2684 - 2689 View in Reaxys Reaction Steps: 2 1: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; C24H23ClCrIrNO3 / dichloromethane / 24 h / 40 °C / Schlenk technique; Glovebox; Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / Inert atmosphere With C24H23ClCrIrNO3, tetrabutyl ammonium fluoride, sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate in tetrahydrofuran, dichloromethane Corre, Yann; Rysak, Vincent; Trivelli, Xavier; Agbossou-Niedercorn, Francine; Michon, Christophe; European Journal of Organic Chemistry; vol. 2017; nb. 32; (2017); p. 4820 - 4826 View in Reaxys With hydrogen, 1,8-diazabicyclo[5.4.0]undec-7-ene in n-heptane, Time= 1h, T= 25 °C , p= 37503.8Torr , Ionic liquid, chemoselective reaction Brünig, Julian; Csendes, Zita; Weber, Stefan; Gorgas, Nikolaus; Bittner, Roland W.; Limbeck, Andreas; Bica, Katharina; Hoffmann, Helmuth; Kirchner, Karl; ACS Catalysis; vol. 8; nb. 2; (2018); p. 1048 - 1051 View in Reaxys

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O N

Rx-ID: 10022951 View in Reaxys 2/69 Yield

Conditions & References

98 %

With sodium tetrahydroborate, sodium methylate in methanol, Time= 3h, T= 25 °C , Inert atmosphere Prasanth; Joseph, Ebbin; Abhijith; Nair; Ibnusaud, Ibrahim; Raskatov, Jevgenij; Singaram, Bakthan; Journal of Organic Chemistry; vol. 83; nb. 3; (2018); p. 1431 - 1440 View in Reaxys With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)], potassium tert-butylate, hydrogen in tetrahydro-

93 %

furan, Time= 5h, T= 50 °C , p= 7500.75Torr , Schlenk technique, Inert atmosphere Ogata, Osamu; Nakayama, Yuji; Nara, Hideki; Fujiwhara, Mitsuhiko; Kayaki, Yoshihito; Organic Letters; vol. 18; nb. 15; (2016); p. 3894 - 3897 View in Reaxys With sodium tetrahydroborate, C36H30F6N10Ni4O10 (2+)*2C2F3O2 (1-), zinc(II) chloride in tetrahydrofuran, Time= 12h, T= 45 °C

89 %

Tsai, Bing-Chen; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; European Journal of Inorganic Chemistry; vol. 2016; nb. 17; (2016); p. 2783 - 2790 View in Reaxys 82 %

Stage 1: With sodium tetrahydroborate in tetrahydrofuran, Time= 0.25h, T= 70 °C Stage 2: in tetrahydrofuran, methanol, Time= 1h, T= 70 °C Boechat, Nubia; Da Costa, Jorge Carlos Santos; De Souza Mendonca, Jorge; Paes, Karla Ceodaro; Fernandes, Elisa Lopes; De Oliveira, Pedro Santos Mello; Vasconcelos, Thatyana Rocha Alves; De Souza, Marcus Vinicius Nora; Synthetic Communications; vol. 35; nb. 24; (2005); p. 3187 - 3190 View in Reaxys

99 %Chromat.

38 : Example 38Hydrogenation of Methyl Picolinate In a 50 mE glass Schlenk tube, 14.2 mg (0.0200 mmol/Ru) of ruthenium complex D produced in Example 5 was added, and after replacement with nitrogen gas, 0.10 mE (0.10 mmol) of 1 M K093u (solution in THF), 3.8 mE of THF, and 137 mg (1.0 mmol) of a substrate were added, and then a balloon containing hydrogen gas was attached to the Schienk tube to conduct replacement with hydrogen gas, and stirred at 50° C. for 6 hours. After cooling, the reactant was analyzed by GC, and 2-pyridinemethanol was obtained with a GC yield of 99percent. With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)], potassium tert-butylate, hydrogen in tetrahydrofuran, Time= 6h, T= 50 °C , Schlenk technique, Concentration, Reagent/catalyst, Solvent, Temperature Patent; Takasago International Corporation; Ogata, Osamu; Nara, Hideki; Nakayama, Yuji; (38 pag.); US2017/44196; (2017); (A1) English View in Reaxys

N O

Rx-ID: 106584 View in Reaxys 3/69 Yield

Conditions & References With hydrogenchloride, water Boekelheide; Linn; Journal of the American Chemical Society; vol. 76; (1954); p. 1286,1289 View in Reaxys With sodium hydroxide, water Maruszewska-Wieczorkowska; Michalski; Roczniki Chemii; vol. 31; (1957); p. 543,547,550; ; (1958); p. 5406 View in Reaxys

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With aq. acid Jones, Gurnos; Sliskovic, D. Robert; Foster, Beverley; Rogers, John; Smith, Anthony K.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 78 - 81 View in Reaxys With sodium hydroxide in methanol, Time= 2h, Ambient temperature Weidmann, Klaus; Herling, Andreas W.; Lang, Hans-Jochen; Scheunemann, Karl-Heinz; Rippel, Robert; et al.; Journal of Medicinal Chemistry; vol. 35; nb. 3; (1992); p. 438 - 450 View in Reaxys With sodium hydroxide in methanol, Heating Kuehler, Thomas C.; Swanson, Marianne; Shcherbuchin, Vladimir; Larsson, Hakan; Mellgard, Bjoern; Sjoestroem, JanEric; Journal of Medicinal Chemistry; vol. 41; nb. 11; (1998); p. 1777 - 1788 View in Reaxys 1 :The -2 - states the ethanoic acid methyl pyridine with potassium hydroxide solution reaction, the potassium hydroxide solution quality percentage is 20percent, the reaction time is 5 h, the acetic acid -2 - pyridine ester with potassium hydroxide in a molar ratio of 1: 1.5, reaction to obtain the 2 - pyridine methanol; With potassium hydoxide, Time= 5h, Concentration Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys

N OH

Rx-ID: 17154151 View in Reaxys 4/69 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -70 °C 2: 1.) iodobenzene bis(trifluoroacetate), 2.) 10percent aq. HCl / 1.) CH2Cl2, r.t., 1 h, 2.) ether With hydrogenchloride, n-butyllithium, bis-[(trifluoroacetoxy)iodo]benzene in tetrahydrofuran, hexane Andrews, Ian P.; Lewis, Norman J.; McKillop, Alexander; Wells, Andrew S.; Heterocycles; vol. 43; nb. 6; (1996); p. 1151 1158 View in Reaxys Reaction Steps: 5 1.1: sulfuric acid / 2.5 h / 70 - 92 °C 2.1: acetic acid / 0.33 h / 85 °C 2.2: 2.5 h / 90 °C 3.1: phosphorus trichloride / chloroform / 1.2 h / 2.5 °C 4.1: iron; ammonium hydroxide / 1 h / 165 °C 5.1: cis-nitrous acid / 1 h / 0 - 2 °C With ammonium hydroxide, sulfuric acid, cis-nitrous acid, iron, acetic acid, phosphorus trichloride in chloroform Patent; Anhui Xingyu Chemical Co., Ltd.; Zhang Sheng; Zhang Kuanyu; Jin Wenyi; Li Jing; (7 pag.); CN107162960; (2017); (A) Chinese View in Reaxys Reaction Steps: 3 1: acetic acid; dihydrogen peroxide / 16 h / 65 °C 2: 5 h / 90 °C 3: potassium hydoxide / 5 h With dihydrogen peroxide, acetic acid, potassium hydoxide Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys

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Si O

Rx-ID: 46099037 View in Reaxys 5/69 Yield

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 12h, Inert atmosphere Corre, Yann; Rysak, Vincent; Trivelli, Xavier; Agbossou-Niedercorn, Francine; Michon, Christophe; European Journal of Organic Chemistry; vol. 2017; nb. 32; (2017); p. 4820 - 4826 View in Reaxys NH 2 N OH

H 2N

Rx-ID: 46501547 View in Reaxys 6/69 Yield

Conditions & References 1.4 : 4) Synthesis of 2-pyridinemethanol Take step 3) obtained 2-chloromethyl-3,5-dinitropyridine 21.76g,To which was added 4.5percent aqueous ammonia to neutralize hydrolysis,Then adding iron powder to it for reduction reaction at 165 DEG C for 1 hour, filtering and decolorizing,Then dilute nitrous acid was added dropwise to the solution to adjust the pH, the reaction was stirred at 0-2 for 1h,Normal rose to room temperature,Then recrystallized with organic reagent to obtain 2-pyridine methanol 10.45g, yield 95.8percent. With cis-nitrous acid, Time= 1h, T= 0 - 2 °C Patent; Anhui Xingyu Chemical Co., Ltd.; Zhang Sheng; Zhang Kuanyu; Jin Wenyi; Li Jing; (7 pag.); CN107162960; (2017); (A) Chinese View in Reaxys N N OH

Rx-ID: 46501553 View in Reaxys 7/69 Yield

Conditions & References Reaction Steps: 4 1.1: acetic acid / 0.33 h / 85 °C 1.2: 2.5 h / 90 °C 2.1: phosphorus trichloride / chloroform / 1.2 h / 2.5 °C 3.1: iron; ammonium hydroxide / 1 h / 165 °C 4.1: cis-nitrous acid / 1 h / 0 - 2 °C With ammonium hydroxide, cis-nitrous acid, iron, acetic acid, phosphorus trichloride in chloroform Patent; Anhui Xingyu Chemical Co., Ltd.; Zhang Sheng; Zhang Kuanyu; Jin Wenyi; Li Jing; (7 pag.); CN107162960; (2017); (A) Chinese View in Reaxys O N

N OH

O N

Rx-ID: 46501557 View in Reaxys 8/69 Yield

Conditions & References Reaction Steps: 3 1: phosphorus trichloride / chloroform / 1.2 h / 2.5 °C 2: iron; ammonium hydroxide / 1 h / 165 °C 3: cis-nitrous acid / 1 h / 0 - 2 °C

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With ammonium hydroxide, cis-nitrous acid, iron, phosphorus trichloride in chloroform Patent; Anhui Xingyu Chemical Co., Ltd.; Zhang Sheng; Zhang Kuanyu; Jin Wenyi; Li Jing; (7 pag.); CN107162960; (2017); (A) Chinese View in Reaxys O N

Rx-ID: 46695158 View in Reaxys 9/69 Yield

Conditions & References Reaction Steps: 2 1: 5 h / 90 °C 2: potassium hydoxide / 5 h With potassium hydoxide Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys O N

Rx-ID: 106399 View in Reaxys 10/69 Yield

Conditions & References

86 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, T= 0 °C , Reflux Radi, Smaail; Tighadouini, Said; Bacquet, Maryse; Degoutin, Stéphanie; Janus, Ludovic; Mabkhot, Yahia N.; RSC Advances; vol. 6; nb. 86; (2016); p. 82505 - 82514 View in Reaxys With lithium aluminium tetrahydride, diethyl ether Micovic; Mihailovic; Recueil des Travaux Chimiques des Pays-Bas; vol. 71; (1952); p. 970,974 View in Reaxys Bohlmann; Bohlmann; Chemische Berichte; vol. 86; (1953); p. 1419,1422 View in Reaxys Simonetta; Favini; Gazzetta Chimica Italiana; vol. 84; (1954); p. 566,572; Gazzetta Chimica Italiana; vol. 85; (1955); p. 1025,1027 View in Reaxys

N OH

Rx-ID: 5409745 View in Reaxys 11/69 Yield 94 %

Conditions & References General procedure: [0179] The reaction of benzaldehyde 4a and phenylsilane 5 was investigated in the presence of various pincer nickel complexes (1.0 molpercent) and benzyl alcohol was obtained in 99percent yield when 2 was employed (Table 1, entry1). Slightly lower yields of benzyl alcohol were observed when complexes 1 and3 were tested with longer reaction time (Table 1, entries 2 and 3). No product was observed without using Ni complexes (Table 1, entry 4). These observations suggested that complexes 1-3 serve as the catalyst and 2 was the best among them. Reaction screenings with various solvents (Table 1, entries 5-7), under different temperatures and catalyst loadings (Table 1, entries 8-11) indicated that 0.2 molpercent of 2 showed satisfactory catalyst performance in toluene at 80 °C. [01 87] General procedures for hydrosilylation of aldehyde: to a flame- dried Schlenk flask was added a solution of nickel PN3P-pincer complex 2 (1.0 mg, 2 imol) in toluene (1.0 mL), an aldehyde substrate (1.0 mmol) and PhSiH3 (49 1iL, 0.4 mmol) under an argon atmosphere. The resulting mixture was stirred at 80 °C until there was no aldehyde left (monitored by withdrawing aliquots and analyzing their ‘H NIVIR spectra). The reaction was then quenched by a 10percent aqueous solution of NaOH (about 1.0 mL) with vigorous stirring for more than 12 hours. The solution containing the alcohol product was extracted with

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diethyl ether three times, dried over anhydrous Na2SO4, and concentrated under vacuum. The desired alcohol was further purified by flash column chromatography. Stage 1: With phenylsilane, C21H41N3NiP2 in toluene, Time= 16h, T= 80 °C , Inert atmosphere Stage 2: With water, sodium hydroxide, Time= 12h Patent; KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY; HUANG, Kuo-wei; ZHAO, Qianyi; (56 pag.); WO2016/38543; (2016); (A1) English View in Reaxys 82 %

23 :General procedure: Examples 6 to 25 [0033] In a stainless steel pressure resistant vessel having an inner capacity of 40 mL equipped with a thermometer and a manometer, the amine shown in Table 2 below was charged along with methanol, water and sodium hydroxide at a molar ratio of amine/methanol/water/sodium hydroxide of 1/110/70/1.4, and the vessel was sealed under a nitrogen atmosphere. The mixture was heated and held at 240°C for 2 hours. After cooling, the reaction solution was taken out, and after neutralizing sodium hydroxide, was analyzed. The results are shown in Table 2. With water, sodium hydroxide in methanol, Time= 2h, T= 240 °C , Inert atmosphere, Autoclave Patent; Mitsubishi Gas Chemical Company, Inc.; KANBARA, Yutaka; ABE, Takafumi; FUSHIMI, Norio; EP2657214; (2013); (A1) English View in Reaxys

78 %

13 Patent; DSM FINE CHEMICALS AUSTRIA NFG GmbH and Co KG; WO2008/77769; (2008); (A1) English View in Reaxys Buratti,W. et al.; Tetrahedron; vol. 27; (1971); p. 3655 - 3668 View in Reaxys Hamana; Yamazaki; Yakugaku Zasshi; vol. 81; (1961); p. 574,575-578; ; nb. 24743; (1961) View in Reaxys Tagaki et al.; Tetrahedron Letters; (1976); p. 2541,2542 View in Reaxys Nakamura et al.; Bulletin of the Chemical Society of Japan; vol. 52; (1979); p. 488,489 View in Reaxys Nakamura et al.; Chemistry Letters; (1977); p. 1203,1204 View in Reaxys Kikugawa et al.; Chemical and Pharmaceutical Bulletin; vol. 21; (1973); p. 1927,1936 View in Reaxys Kuwata; Bulletin of the Chemical Society of Japan; vol. 33; (1960); p. 1672,1676 View in Reaxys Jones; Russell; Journal of the Chemical Society [Section] C: Organic; (1969); p. 2246 View in Reaxys Oda; Nippon Kagaku Zasshi; vol. 82; (1961); p. 478; ; vol. 56; nb. 10089; (1962) View in Reaxys Voegtle et al.; Journal of Chemical Research, Miniprint; (1978); p. 4848,4851 View in Reaxys Hata; Bulletin of the Chemical Society of Japan; vol. 34; (1961); p. 1440 View in Reaxys Murakami; Takagi; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 828,829 View in Reaxys Udovenko et al.; Sov. Prog. Chem. (Engl. Transl.); vol. 38; nb. 11; (1972); p. 1120,39 View in Reaxys Deegan; Rose; Journal of the Chemical Society [Section] C: Organic; (1971); p. 2756,2760 View in Reaxys Murakami et al.; Bulletin of the Chemical Society of Japan; vol. 39; (1966); p. 1197,1199 View in Reaxys Dregval; Rybak; Khimiya Geterotsiklicheskikh Soedinenii; (1967); p. 227; ; vol. 70; nb. 87501f; (1969) View in Reaxys Chumakov; Stolyarov; Metody Polucheniya Khimicheskikh Reaktivov i Preparatov; vol. 7; (1963); p. 65,66-69; ; vol. 61; nb. 10652h; (1964) View in Reaxys Kazarinova et al.; Metody Polucheniya Khimicheskikh Reaktivov i Preparatov; vol. 14; (1966); p. 98,99; ; vol. 67; nb. 32560

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View in Reaxys Patent; Udovenko et al.; SU276959; (1970); Ref. Zh., Khim.; vol. 11; nb. N197P; (1971) View in Reaxys Kriwoschtschekowa; Schamschurin; Biol. Akt. Soedin.; (1968); p. 110 - 112; ; vol. 71; nb. 124151; (1969) View in Reaxys Krivoshchekova; Shamshurin; Biol. Akt. Soedin.; (1968); p. 110; ; vol. 71; nb. 124151k; (1969) View in Reaxys Patent; Hitachi Chemical. Co.; DE2008443; (1970); ; vol. 74; nb. 3400 View in Reaxys Hughes; Prince; Journal of Inorganic and Nuclear Chemistry; vol. 40; (1978); p. 719,720-722 View in Reaxys Huang; Chen; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 21; (1974); p. II-235,236,238 View in Reaxys Still other representative azoxy-dentated ligands, that is non-acidic azoxy-dentated ligands, useful in the present invention include: N,n,n',n'-tetra-(2-hydroxyethyl)ethylenediamine; N,n,n',n'-tetra(2-hydroxypropyl)ethylenediamine; N,n'-di-(2-hydroxyethyl)ethylenediamine; 2-hydroxymethylpyridine; 8-hydroxyquinoline; 8-hydroxy-2-methylquinoline; o-aminophenol; N-(3-aminopropyl)diethanolamine; Patent; Chevron Research Company; US4142061; (1979); (A) English View in Reaxys

N O

Rx-ID: 43108540 View in Reaxys 12/69 Yield

Conditions & References

57 %

With methyldiphenylsilane, palladium on activated charcoal in water, acetonitrile, Time= 9h, T= 80 °C , p= 7500.75Torr Molla, Rostam Ali; Iqubal, Md. Asif; Ghosh, Kajari; Islam, Sk Manirul; Green Chemistry; vol. 18; nb. 17; (2016); p. 4649 4656 View in Reaxys

O Si

N OH

Rx-ID: 44122760 View in Reaxys 13/69 Yield

Conditions & References With sodium hydroxide in methanol, water, Time= 24h, T= 60 °C , Schlenk technique, Inert atmosphere Zheng, Tingting; Li, Junye; Zhang, Shumiao; Xue, Benjing; Sun, Hongjian; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter; Organometallics; vol. 35; nb. 20; (2016); p. 3538 - 3545 View in Reaxys

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O N

SiH

Rx-ID: 41247285 View in Reaxys 14/69 Yield

Conditions & References

97.1 mg

With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 3h, T= 0 - 20 °C Wekesa, Francis S.; Arias-Ugarte, Renzo; Kong, Lydia; Sumner, Zachary; McGovern, Gregory P.; Findlater, Michael; Organometallics; vol. 34; nb. 20; (2015); p. 5051 - 5056 View in Reaxys

Rx-ID: 37689895 View in Reaxys 15/69 Yield

Conditions & References

82 %, 6 %

With palladium 10 on activated carbon, zinc in ethanol, water, Time= 24h, T= 150 °C , Autoclave Abarca, Belen; Adam, Rosa; Alom, Shamim; Ballesteros, Rafael; Lopez-Molina, Sonia; Arkivoc; vol. 2014; nb. 2; (2014); p. 175 - 186 View in Reaxys O N

Rx-ID: 38200474 View in Reaxys 16/69 Yield

Conditions & References With hydrogen bromide, magnesium in tetrahydrofuran, diethyl ether, Time= 0.5h, T= 0 - 50 °C , Inert atmosphere, Schlenk technique Kamitani, Masahiro; Ito, Masaki; Itazaki, Masumi; Nakazawa, Hiroshi; Chemical Communications; vol. 50; nb. 59; (2014); p. 7941 - 7944 View in Reaxys

NH 2

Rx-ID: 45860 View in Reaxys 17/69 Yield 75 %

Conditions & References With sodium hydroxide in methanol, water, Time= 2h, T= 240 °C , Autoclave, Inert atmosphere Kanbara, Yutaka; Abe, Takafumi; Fushimi, Norio; Ikeno, Taketo; Synlett; vol. 23; nb. 5; (2012); p. 706 - 710 View in Reaxys With hydrogenchloride, silver(I) nitrite Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys

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Rx-ID: 33824583 View in Reaxys 18/69 Yield

Conditions & References

83 %

Typical procedures: 6-bromonicotinaldehyde (930 mg, 5.0 mmol), NaOAc (820 mg, 10.0 mmol), MeOH (30 mL), and PdCl2 (45 mg) were mixed in a glass bottle capped with a balloon filled with hydrogen. After stirred at 35 °C for 4 h, the mixture was filtered and washed with MeOH. The solvent was removed and the residue was dissolved in water, neutralized with solid NaHCO3, and extracted with ethyl acetate. The organic phase was dried over anhyd Na2SO4, and then filtered. The solvent was removed and the residue was subjected to chromatography to yield pyridin-3-ylmethanol (428 mg, 78percent). With hydrogen, sodium acetate, palladium dichloride in methanol, Time= 4h, T= 35 °C , p= 760.051Torr Chen, Xi-Bo; Hu, Qiu-Peng; Yuan, Qian-Jia; Ding, Wei; Ren, Jiangmeng; Zeng, Bu-Bing; Tetrahedron Letters; vol. 53; nb. 29; (2012); p. 3798 - 3801 View in Reaxys

Rx-ID: 28381886 View in Reaxys 19/69 Yield

Conditions & References 1.3 :2-Chloromethylpyridine hydrochloride (10.9 mmol) is dissolved in 15 water and NaOH (32 percent in water) is added and extracted with dichloromethane. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. The remaining residue is added to a suspension of NaH (2 eq.) in DMF at 0 0C. Afterwards 2-(1H-Pyrazole-3- yl)-isoindole-1 ,3dione (11.7 mmol) is added and the reaction is stirred 15 hours at 50 0C. The solvent is removed in vacuo. Hydrazine hydroxide (20 ml) and ethanol (20 ml) is added and the reaction is stirred 3 days at 120 0C. The solvent is removed in vacuo and the residue is suspended in dichloromethane and filtrated. The solvent of the filtrate is removed in vacuo. The remaining residue is purified via column chromatography (ethyl acetate / methanol). 1-Pyridine-2-ylmethyl-1H-pyrazole-3-ylamine is isolated as a yellow powder in a yield of 20 percent; HPLC (Method B): 0.49 min; LG-MS- 0-550 min, 175.15 (M+H+);30 1 H-NMR (DMSO-d6, 400 MHz): η [ppm] 8.509-8.493 (m, 1 H), 7.754-7.711 (m, 1H), 7.466 (d, 1H, J=2.2 Hz), 7.285-7.251 (m, 1 H), 6.943-6.924 (m, 1H), 5.447 (d, 1H, J=2.2 Hz), 5.118 (s, 2H), 4.574 (s, 2H). With sodium hydroxide in water, Alkaline aqueous solution Patent; MERCK PATENT GMBH; WO2009/46802; (2009); (A1) English View in Reaxys

O N OH

Rx-ID: 27964115 View in Reaxys 20/69 Yield

Conditions & References

73 %

With sodium methylate in methanol, Time= 12h, T= 20 °C Hasnik, Zbynek; Silhar, Peter; Hocek, Michal; Synlett; nb. 4; (2008); p. 543 - 546 View in Reaxys N N OH

N O

Rx-ID: 11110462 View in Reaxys 21/69

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Yield

Conditions & References With pig liver esterase, 1,4-dihydronicotinamide adenine dinucleotide, horse liver alcohol dehydrogenase in phosphate buffer, acetonitrile, pH= 7 Hamberg, Anders; Lundgren, Stina; Wingstrand, Erica; Moberg, Christina; Hult, Karl; Chemistry - A European Journal; vol. 13; nb. 15; (2007); p. 4334 - 4341 View in Reaxys 2 HCl

OH HO

P O

Rx-ID: 11174545 View in Reaxys 22/69 Yield

Conditions & References

30 %

With hydrogenchloride, hypophosphorous acid, Time= 2h, Heating Olszewski, Tomasz Krzysztof; Galezowska, Joanna; Boduszek, Bogdan; Kozlowski, Henryk; European Journal of Organic Chemistry; nb. 21; (2007); p. 3539 - 3546 View in Reaxys OH

PH (v5)

Rx-ID: 11174548 View in Reaxys 23/69 Yield

Conditions & References With sulfuric acid, T= 75 - 95 °C , Kinetics Olszewski, Tomasz Krzysztof; Galezowska, Joanna; Boduszek, Bogdan; Kozlowski, Henryk; European Journal of Organic Chemistry; nb. 21; (2007); p. 3539 - 3546 View in Reaxys O

Rx-ID: 10271462 View in Reaxys 24/69 Yield

Conditions & References

39 %, 36 %

With N,N,N',N'-tetramethylguanidine in water, Time= 7h, T= 20 °C , Cannizzaro reaction Basavaiah, Deevi; Sharada, Duddu S.; Veerendhar, Ainelly; Tetrahedron Letters; vol. 47; nb. 32; (2006); p. 5771 - 5774 View in Reaxys

O N

N N

Rx-ID: 10138171 View in Reaxys 25/69 Yield 72 %

Conditions & References With sodium tetrahydroborate in methanol, Time= 0.5h, T= 20 °C Singh, Kamal Nain; Kaur, Amarjit; Synthetic Communications; vol. 35; nb. 22; (2005); p. 2935 - 2937 View in Reaxys

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O N OH

Rx-ID: 10331933 View in Reaxys 26/69 Yield

Conditions & References

95 %

With sodium hydroxide in methanol, Time= 0.0833333h, T= 20 °C Ko, Sangwon; Na, Youngim; Chang, Sukbok; Journal of the American Chemical Society; vol. 124; nb. 5; (2002); p. 750 - 751 View in Reaxys

NH N

O O N

Rx-ID: 10241752 View in Reaxys 27/69 Yield

Conditions & References

70 % Chromat.

With ammonium formate, dodecacarbonyl-triangulo-triruthenium in toluene, Time= 20h, T= 160 °C , Product distribution Chatani; Tatamidani; Ie; Kakiuchi; Murai; Journal of the American Chemical Society; vol. 123; nb. 20; (2001); p. 4849 4850 View in Reaxys

O O

Rx-ID: 10248268 View in Reaxys 28/69 Yield

Conditions & References

95 % Chromat.

With ammonium formate, dodecacarbonyl-triangulo-triruthenium in 1,4-dioxane, Time= 40h, T= 160 °C , Product distribution, Further Variations: Solvents, Reagents Chatani; Tatamidani; Ie; Kakiuchi; Murai; Journal of the American Chemical Society; vol. 123; nb. 20; (2001); p. 4849 4850 View in Reaxys

O O N OH

Rx-ID: 10282038 View in Reaxys 29/69 Yield 90 % Chromat.

Conditions & References With ammonium formate, dodecacarbonyl-triangulo-triruthenium in 1,4-dioxane, Time= 20h, T= 160 °C , Product distribution Chatani; Tatamidani; Ie; Kakiuchi; Murai; Journal of the American Chemical Society; vol. 123; nb. 20; (2001); p. 4849 4850 View in Reaxys

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N OH

Rx-ID: 10331914 View in Reaxys 30/69 Yield

Conditions & References

78 % Chromat.

With ammonium formate, dodecacarbonyl-triangulo-triruthenium in 1,4-dioxane, Time= 20h, T= 160 °C , Product distribution Chatani; Tatamidani; Ie; Kakiuchi; Murai; Journal of the American Chemical Society; vol. 123; nb. 20; (2001); p. 4849 4850 View in Reaxys O N

Rx-ID: 10331928 View in Reaxys 31/69 Yield

Conditions & References

76 % Chromat.

Rx-ID: 3942859 View in Reaxys 32/69 Yield

Conditions & References

58 %, 24 %

With diethylzinc, (S)-(-)-2-lt;2',2'-dimethyl-1'-(2''-pyridyl)propoxygt;-1,1-di-(η-naphthyl)ethanol in hexane, toluene, Time= 0.00833333h, Ambient temperature Ishizaki, Miyuki; Hoshino, Osamu; Chemistry Letters; nb. 7; (1994); p. 1337 - 1340 View in Reaxys

40 %, 50 %

With ethylmagnesium bromide in diethyl ether, Time= 2h, T= 0 °C Uenishi, Jun'ichi; Hiraoka, Takao; Hata, Shinichiro; Nishiwaki, Kenji; Yonemitsu, Osamu; Nakamura, Kaoru; Tsukube, Hiroshi; Journal of Organic Chemistry; vol. 63; nb. 8; (1998); p. 2481 - 2487 View in Reaxys OH

Mg Br

Rx-ID: 4978657 View in Reaxys 33/69 Yield 40 %, 50 %

Conditions & References in diethyl ether, Time= 2h, T= 0 °C Uenishi, Jun'ichi; Hiraoka, Takao; Hata, Shinichiro; Nishiwaki, Kenji; Yonemitsu, Osamu; Nakamura, Kaoru; Tsukube, Hiroshi; Journal of Organic Chemistry; vol. 63; nb. 8; (1998); p. 2481 - 2487 View in Reaxys

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Mg Br

Rx-ID: 4978658 View in Reaxys 34/69 Yield

Conditions & References

40 %

in diethyl ether, Time= 2h, T= 0 °C , Yield given Uenishi, Jun'ichi; Hiraoka, Takao; Hata, Shinichiro; Nishiwaki, Kenji; Yonemitsu, Osamu; Nakamura, Kaoru; Tsukube, Hiroshi; Journal of Organic Chemistry; vol. 63; nb. 8; (1998); p. 2481 - 2487 View in Reaxys

Rx-ID: 4760017 View in Reaxys 35/69 Yield

Conditions & References With hydrogenchloride, bis-[(trifluoroacetoxy)iodo]benzene, 1.) CH2Cl2, r.t., 1 h, 2.) ether, Yield given. Multistep reaction Andrews, Ian P.; Lewis, Norman J.; McKillop, Alexander; Wells, Andrew S.; Heterocycles; vol. 43; nb. 6; (1996); p. 1151 1158 View in Reaxys O N

O F

Rx-ID: 4186801 View in Reaxys 36/69 Yield

Conditions & References With potassium carbonate in dichloromethane, Time= 3h, Yield given Fontenas; Bejan; Haddou; Balavoine; Synthetic Communications; vol. 25; nb. 5; (1995); p. 629 - 633 View in Reaxys OH

(v2)

Rx-ID: 3942845 View in Reaxys 37/69 Yield

Conditions & References

24 %, 58 %

With (S)-(-)-2-lt;2',2'-dimethyl-1'-(2''-pyridyl)propoxygt;-1,1-di-(η-naphthyl)ethanol in hexane, toluene, Time= 0.00833333h, Ambient temperature Ishizaki, Miyuki; Hoshino, Osamu; Chemistry Letters; nb. 7; (1994); p. 1337 - 1340 View in Reaxys O

N O

Rx-ID: 4185871 View in Reaxys 38/69 Yield

Conditions & References With sodium methylate in methanol, Time= 3h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Kinoshita; Ohishi; Journal of Heterocyclic Chemistry; vol. 31; nb. 6; (1994); p. 1599 - 1603 View in Reaxys

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Rx-ID: 4241053 View in Reaxys 39/69 Yield

Conditions & References

14 %, 66 %

With hydrogen, GIPKh-105 copper-chromium catalyst, T= 200 °C , other isomeric pyridinecarboxaldehydes; var. temp., Product distribution, Mechanism Yansone, D. P.; Stonkus, V. V.; Leitis, La. Ya.; Fleisher, M. B.; Shimanska, M.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 30; nb. 8; (1994); p. 934 - 937; Khimiya Geterotsiklicheskikh Soedinenii; nb. 8; (1994); p. 1082 1086 View in Reaxys

NH 2 N

Rx-ID: 1574046 View in Reaxys 40/69 Yield

Conditions & References

24 %, 62 %

With samarium diiodide in tetrahydrofuran, Time= 0.583333h, Ambient temperature Kamochi; Kudo; Tetrahedron; vol. 48; nb. 21; (1992); p. 4301 - 4312 View in Reaxys

N OH

NH 2

Rx-ID: 2098556 View in Reaxys 41/69 Yield

Conditions & References

33 %, 1 %, 18 %

With samarium diiodide, phosphoric acid in tetrahydrofuran, Time= 0.000833333h, Ambient temperature, other amides; also without H3PO4, Product distribution, Mechanism Kamochi; Kudo; Tetrahedron; vol. 48; nb. 21; (1992); p. 4301 - 4312 View in Reaxys

O N H

N OH

HN O

Rx-ID: 3482482 View in Reaxys 42/69 Yield

Conditions & References With cobalt(II) in 1,4-dioxane, water, T= 50 °C , Rate constant Fife, Thomas H.; Przystas, Theodore J.; Pujari, Mahesh P.; Journal of the American Chemical Society; vol. 110; (1988); p. 8157 - 8163 View in Reaxys

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O NH 2

N OH

NH 2

O N

Rx-ID: 1523489 View in Reaxys 43/69 Yield

Conditions & References

12 %, 55 %, With tris(2,2'-bipyridyl)ruthenium dichloride in methanol, Time= 2h, Irradiation 4% Ishitani, Osamu; Yanagida, Shozo; Takamuku, Setsuo; Pac, Chyongjin; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2790 - 2796 View in Reaxys

O NH 2

O N OH

NH 2

Rx-ID: 1523929 View in Reaxys 44/69 Yield

Conditions & References

12 %, 55 %, With tris(2,2'-bipyridyl)ruthenium dichloride, 1-Benzyl-1,4-dihydronicotinamide in methanol, Time= 2h, Irradiation 4% Ishitani, Osamu; Yanagida, Shozo; Takamuku, Setsuo; Pac, Chyongjin; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2790 - 2796 View in Reaxys

Rx-ID: 2155162 View in Reaxys 45/69 Yield

Conditions & References

78 %

With sulfuric acid in water, Time= 5h, T= 95 °C Jones, Gurnos; Mouat, Deborah J.; Tonkinson, Daryl J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2719 - 2724 View in Reaxys

N O O (v1) OHO N(v4) N (v4) (v4)N (v4)N Co(v6) O HO (v4)(v1) N

Rx-ID: 26852613 View in Reaxys 46/69

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Yield

Conditions & References

14 %, 86 %

in methanol, decomposition of the complex by refluxing in methanol under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compounds with ether, gas chromatography Gupta, B. D.; Roy, Sujit; Inorganica Chimica Acta; vol. 108; (1985); p. 261 - 264 ; (from Gmelin) View in Reaxys

N+

NH 2

Rx-ID: 1523663 View in Reaxys 47/69 Yield

Conditions & References

98 %

With zinc(II) chloride, Time= 15h, T= 50 °C , in the dark, pH 4.7; further reducing agent, Rate constant, Mechanism Tabushi, Iwao; Kuroda, Yasuhisa; Mizutani, Tadashi; Journal of the American Chemical Society; vol. 106; nb. 11; (1984); p. 3377 - 3378 View in Reaxys

N+

H N

Rx-ID: 1523783 View in Reaxys 48/69 Yield

Conditions & References

96 %

N OH

Rx-ID: 1561012 View in Reaxys 49/69 Yield

Conditions & References Irradiation, Co-60 η-rays Sugimori, Akira; Mori, Shoji; Maeda, Kazuo; Nishijima, Masayuki; Chemistry Letters; (1984); p. 769 - 772 View in Reaxys

O NH 2

N OH

NH 2

Rx-ID: 1523487 View in Reaxys 50/69 Yield 20 %, 33 %

Conditions & References With tris(2,2'-bipyridyl)ruthenium dichloride in methanol, Time= 20h, Irradiation Ishitani, Osamu; Pac, Chyongjin; Sakurai, Hiroshi; Journal of Organic Chemistry; vol. 48; nb. 17; (1983); p. 2941 - 2942 View in Reaxys

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O N

N OH

N N

Rx-ID: 1540137 View in Reaxys 51/69 Yield

Conditions & References T= 500 - 800 °C , p= 0.01 - 0.1Torr , other pyridine and pyridazine N-oxides, Product distribution Kawaguchi, Takayuki; Ohsawa, Akio; Igeta, Hiroshi; Heterocycles; vol. 20; nb. 1; (1983); p. 125 View in Reaxys

N HO

H racemate

Rx-ID: 1523913 View in Reaxys 52/69 Yield

Conditions & References With sodium hydroxide, titanium(III) chloride in water, acetic acid, Time= 7h, Ambient temperature, Yield given. Yields of byproduct given Clerici, Angelo; Porta, Ombretta; Tetrahedron; vol. 38; nb. 9; (1982); p. 1293 - 1297 View in Reaxys N

Rx-ID: 1561013 View in Reaxys 53/69 Yield

Conditions & References

8 %, 15 %

With sulfuric acid, Time= 24h, Irradiation Sugimori, Akira; Furihata, Toshikazu; Mikayama, Shigeyuki; Yoshida, Makiko; Nakanishi, Yasuo; Bulletin of the Chemical Society of Japan; vol. 55; nb. 9; (1982); p. 2906 - 2910 View in Reaxys

9 %, 9 %

N OH

Rx-ID: 1561027 View in Reaxys 54/69 Yield 15 %, 7 %

Conditions & References With sulfuric acid, Time= 1h, Irradiation, other alcohol, var. acid, var. acid conc., var. quenchers, var. substrate conc., var. additives, Product distribution, Mechanism Sugimori, Akira; Furihata, Toshikazu; Mikayama, Shigeyuki; Yoshida, Makiko; Nakanishi, Yasuo; Bulletin of the Chemical Society of Japan; vol. 55; nb. 9; (1982); p. 2906 - 2910 View in Reaxys

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Rx-ID: 1561639 View in Reaxys 55/69 Yield

Conditions & References

59 %

With dihydrogen peroxide in formic acid, Time= 12h, Heating Barnes, John H.; Hartley, Frank R.; Jones, Christopher E. L.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3277 - 3280 View in Reaxys

15 %

With dihydrogen peroxide in acetic acid, Time= 12h, T= 80 °C , variation of solvents and reaction time, Product distribution Barnes, John H.; Hartley, Frank R.; Jones, Christopher E. L.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3277 - 3280 View in Reaxys NH 2 N

Rx-ID: 1574047 View in Reaxys 56/69 Yield

Conditions & References With sulfuric acid, isopropyl alcohol, Time= 0.5h, Irradiation Sugimori, Akira; Nishijima, Masayuki; Itoh, Hiroshi; Bulletin of the Chemical Society of Japan; vol. 55; nb. 9; (1982); p. 3055 - 3056 View in Reaxys O

Rx-ID: 1523493 View in Reaxys 57/69 Yield

Conditions & References

47 % Chromat., 44 % Chromat.

With sodium carbonate, rhodium(III) chloride, triphenylphosphine, Time= 48h, Heating Grigg, Ronald; Mitchell, Thomas R. B.; Sutthivaiyakit, Somyote; Tetrahedron; vol. 37; nb. 24; (1981); p. 4313 - 4319 View in Reaxys O

Rx-ID: 1523912 View in Reaxys 58/69 Yield

Conditions & References

47 % Chromat., 44 % Chromat.

With ethanol, sodium carbonate, rhodium(III) chloride, triphenylphosphine, Time= 48h, Heating Grigg, Ronald; Mitchell, Thomas R. B.; Sutthivaiyakit, Somyote; Tetrahedron; vol. 37; nb. 24; (1981); p. 4313 - 4319 View in Reaxys O

O Hg

N OH

(v2)

N O

Rx-ID: 2841995 View in Reaxys 59/69 Yield

Conditions & References With sodium hydroxide, sodium tetrahydroborate, Time= 1h

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Jones, Gurnos; Sliskovic, D. Robert; Foster, Beverley; Rogers, John; Smith, Anthony K.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 78 - 81 View in Reaxys

N OH

Rx-ID: 1530895 View in Reaxys 60/69 Yield

Conditions & References With n-butyllithium, 1) pentane, -20 degC -> room temp., 6 h, 2) -80 degC -> room temp., Yield given. Multistep reaction Meyer, Norbert; Seebach, Dieter; Chemische Berichte; vol. 113; nb. 4; (1980); p. 1290 - 1303 View in Reaxys

O N

HO N

Rx-ID: 2556158 View in Reaxys 61/69 Yield

Conditions & References With water in alkaline medium in acetone, Ambient temperature, Rate constant Sawada, Masami; Ichihara, Masaharu; Ando, Takashi; Yukawa, Yasuhide; Tsuno, Yuho; Tetrahedron Letters; vol. 21; (1980); p. 4917 - 4920 View in Reaxys OH

N OH

O O OH

Rx-ID: 2848562 View in Reaxys 62/69 Yield

Conditions & References With potassium chloride, water, nickel(II), T= 90 °C , other metal ions and temperatures, Rate constant Fife, Thomas H.; Przystas, Theodore J.; Journal of the American Chemical Society; vol. 102; nb. 24; (1980); p. 7297 - 7300 View in Reaxys OH

N OH

Rx-ID: 5474503 View in Reaxys 63/69 Yield

Conditions & References Aufbewahren an feuchter Luft Sauermilch; Chemische Berichte; vol. 90; (1957); p. 833 View in Reaxys

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O O

N OH

Rx-ID: 36950 View in Reaxys 64/69 Yield

Conditions & References Erhitzen des Reaktionsprodukts mit wss. Salzsaeure KOBAYASHI; FURUKAWA; Pharmaceutical bulletin; vol. 1; nb. 4; (1953); p. 347 - 349 View in Reaxys OKUDA; Pharmaceutical bulletin; vol. 3; nb. 4; (1955); p. 316 - 318 View in Reaxys

N OH

2-bromomethyl-pyridine picrate Rx-ID: 5409747 View in Reaxys 65/69 Yield

Conditions & References With water Hasegawa; Pharmaceutical Bulletin; vol. 1; (1953); p. 293,296 View in Reaxys O N

LiAlH4

Rx-ID: 5409748 View in Reaxys 66/69 Yield

Conditions & References Bohlmann; Bohlmann; Chemische Berichte; vol. 86; (1953); p. 1419,1422 View in Reaxys

carbon dioxide free air

N N

Rx-ID: 5434585 View in Reaxys 67/69 Yield

Conditions & References With diethyl ether Edwards; Teague; Journal of the American Chemical Society; vol. 71; (1949); p. 3548 View in Reaxys O N

N OH

Rx-ID: 50278 View in Reaxys 68/69 Yield

Conditions & References With acetic acid, zinc Sorm; Sedivy; Collection of Czechoslovak Chemical Communications; vol. 13; (1948); p. 289,292, 296 View in Reaxys

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N OH

η-pyridinaldehyde Rx-ID: 5409746 View in Reaxys 69/69 Yield

Conditions & References With potassium hydroxide Harries; Lenart; Justus Liebigs Annalen der Chemie; vol. 410; (1915); p. 111 View in Reaxys

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