2-Chloropyridine by Asch

Reaxys

PubChem

eMolecules

Reactions (125)

Yield

Substances (7)

Citations (118)

Conditions

References

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With chlorine

T=220°C; UV-irradiation; Product distribution / selectivity; Hide Experimental Procedure

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Rx-ID: 22301 Find similar reactions

SUMITOMO SEIKA CHEMICALS CO., LTD.

Patent: US2010/324299 A1, 2010 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

EXAMPLE 3; Crude pyridine (1000 g; purity: 99.53percent, imine content:1000 ppm, and aldehyde content: 2600 ppm) and 0.6 g of 98percent aqueous sulfuric acid solution were added to a 2000-mL four-necked flask equipped with a stirrer, condenser tube, thermometer, and dropping funnel, and stirred at 40° C. for 1 hour. Then, 1.6 g of 48percent aqueous sodium hydroxide solution was added and stirred at 40° C. for 4 hours. Subsequently, simple distillation was performed, thereby obtaining 986 g of purified pyridine. The purity of the obtained purified pyridine was 99.82percent (water: 0percent, imine content: 25 ppm, and aldehyde content: 60 ppm).The obtained purified pyridine was subjected to a photochlorination reaction in the same manner as in Example 1. Thus, 128.5 g (1.13 mol) of 2-chloropyridine was obtained. The yield of the obtained 2chloropyridine was 29.7percent with respect to the purified pyridine. With sulfuryl dichloride

T=350°C; Leiten durch Glasrohr;

Pittsburgh Coke and Chem. Co.

Patent: US2839534 , 1956 ; Full Text Show Details

Synthesize Find similar 43%

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Rx-ID: 31472 Find similar reactions

With N-chlorosuccinimide; triphenylphosphine in 1,4dioxane

4 h; Heating;

Sugimoto, Osamu; Mori, Miho; Moriya, Keisuke; Tanji, Ken-Ichi

Helvetica Chimica Acta, 2001 , vol. 84, # 5 p. 1112 - 1118 Title/Abstract Full Text View citing articles Show Details

With phosphorus pentachloride; trichlorophosphate

T=130°C;

v. Pechmann; Baltzer Chemische Berichte, 1891 , vol. 24, p. 3150 Full Text Show Details

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Rx-ID: 32361 Find similar reactions

95%

With hydrogenchloride; N2O3; tetrabutylammonium chloride in dichloromethane

2 h; Ambient temperature;

Daasbjerg, Kim; Lund, Henning

Acta Chemica Scandinavica, 1992 , vol. 46, # 2 p. 157 - 162 Title/Abstract Full Text Show Details

64 % Chromat.

With tert-Butyl thionitrate; copper dichloride in acetonitrile

T=25°C; 0.025 h; other copper(II) halide, other reagent; Product distributionMechanism;

Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae

Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 4 p. 1065 - 1069 Title/Abstract Full Text Show Details

With hydrogenchloride; sodium nitrite

Tschitschibabin; Rjasanzew

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915 , vol. 47, p. 1575 Chem. Zentralbl., 1916 , vol. 87, # II p. 228 Full Text Show Details

Marckwald

Chemische Berichte, 1894 , vol. 27, p. 1323 Full Text Show Details

Hide Details 64 % Chromat.

With tert-Butyl thionitrate; copper dichloride in acetonitrile

T=25°C; 0.025 h;

Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae

Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 4 p. 1065 - 1069 Title/Abstract Full Text Show Details

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Rx-ID: 32401 Find similar reactions

T=140°C; Erhitzen des Reaktionsgemisches auf 250grad;

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Coe et al.

Journal of the Chemical Society, 1957 , p. 323,325 Full Text Show Details

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Rx-ID: 44973 Find similar reactions

With toluene

T=170°C;

Raeth

Justus Liebigs Annalen der Chemie, 1931 , vol. 486, p. 71,78 Full Text Show Details

T=120°C;

Degussa

Patent: US1855119 , 1927 ;

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Full Text Show Details

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Rx-ID: 44982 Find similar reactions

T=170°C;

Raeth

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Archiv der Pharmazie (Weinheim, Germany), 1931 , vol. 486, p. 71,76 Full Text Show Details

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Rx-ID: 44985 Find similar reactions

With phosphorus pentachloride; trichlorophosphate

T=160°C;

Fargher; Furness

Journal of the Chemical Society, 1915 , vol. 107, p. 695 Full Text Show Details

Steinhaeuser; Diepolder

Journal fuer Praktische Chemie (Leipzig), 1916 , vol. <2> 93, p. 395 Full Text Show Details

With trichlorophosphate

Sugasawa; Akaboshi

Proceedings of the Japan Academy, 1952 , vol. 28, p. 296 Full Text Show Details

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Rx-ID: 44992 Find similar reactions

With toluene

T=180°C;

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Raeth

Justus Liebigs Annalen der Chemie, 1931 , vol. 486, p. 71,78 Full Text Show Details

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Rx-ID: 81331 Find similar reactions

Find similar

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Rice; Londergan

Journal of the American Chemical Society, 1955 , vol. 77, p. 4678 Full Text View citing articles Show Details

Alexander et al.

Journal of the American Chemical Society, 1950 , vol. 72, p. 2760 Full Text View citing articles Show Details

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Rx-ID: 81343 Find similar reactions

T=550°C;

Rice; Londergan

Journal of the American Chemical Society, 1955 , vol. 77, p. 4678 Full Text View citing articles Show Details

T=550°C; Leiten durch Glasrohr;

Rice; Londergan

Journal of the American Chemical Society, 1955 , vol. 77, p. 4678 Full Text View citing articles Show Details

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Rx-ID: 1504719 Find similar reactions

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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With trichlorophosphate

T=110°C; 2 h; Yield given. Yields of byproduct given;

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Yamanaka, Hiroshi; Araki, Tomio; Sakamoto, Takao

Chemical and Pharmaceutical Bulletin, 1988 , vol. 36, p. 2244 - 2247 Title/Abstract Full Text Show Details

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Rx-ID: 1526210 Find similar reactions

A: 3% B: 24% C: 29% D: 44%

T=550°C;

Busby, Reginald E.; Hussain, Syed M.; Mohamed, Murtedza bin; Parrick, John; Shaw, C. J. Granville; et al.

Journal of Chemical Research, Miniprint, 1980 , # 12 p. 4935 - 4953 Title/Abstract Full Text Show Details

A: 3% B: 24% C: 29% D: 44%

T=550°C;

Busby, Reginald E.; Hussain, Syed M.; Mohamed, Murtedza bin; Parrick, John; Shaw, C. J. Granville; et al.

Journal of Chemical Research, Miniprint, 1980 , # 12 p. 4935 - 4953 Title/Abstract Full Text Show Details

A: 3% B: 24% C: 29% D: 44%

T=550°C;

Busby, Reginald E.; Hussain, Syed M.; Mohamed, Murtedza bin; Parrick, John; Shaw, C. J. Granville; et al.

Journal of Chemical Research, Miniprint, 1980 , # 12 p. 4935 - 4953 Title/Abstract Full Text Show Details

Synthesize Find similar Rx-ID: 1531140 Find similar reactions

A: 14 % Chromat. B: 16 % Chromat.

With dichloromethane

1 h; Ambient temperatureIrradiation; Title compound not separated from byproducts;

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Ohkura, Kazue; Seki, Koh-ichi; Terashima, Masanao; Kanaoka, Yuichi

Tetrahedron Letters, 1989 , vol. 30, # 26 p. 3433 - 3436 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1531142 Find similar reactions

With dichloromethane

Irradiation; Yield given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

With chloro(1,5-cyclooctadiene) (pentamethylcyclopentadiene)ruthenium(II) in dichloromethane-d2

T=20°C;

Bednářová, Eva; Colacino, Evelina; Lamaty, Frédéric; Kotora, Martin

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 12 p. 1916 - 1923 Title/Abstract Full Text View citing articles Show Details

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40%

With N,N-dimethylformamide; trichlorophosphate

T=80°C; 2 h;

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Rx-ID: 1565229 Find similar reactions

Lai, Long-Li; Lin, Pen-Yuan; Wang, Jy-Shih; Hwu, Jih Ru; Shiao, Min-Jen; Tsay, Shwu-Chen

Journal of Chemical Research - Part S, 1996 , # 4 p. 194 - 195 Title/Abstract Full Text View citing articles Show Details

39%

With N,N-dimethylformamide; trichlorophosphate

0 deg C, 1 h; 80 deg C, 2 h;

Kasturi; Jois; Mathew

Synthesis, 1984 , vol. NO. 9, p. 743 - 746 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1569628 Find similar reactions

95%

With cerium(III) chloride heptahydrate; zinc in methanol

T=20°C; 0.5 h;

Yoo, Byung Woo; Jung, Ha Il; Kim, Se Heon; Ahn, Young Sun; Choi, Ji Yong

Bulletin of the Korean Chemical Society, 2013 , vol. 34, # 2 p. 359 - 360 Title/Abstract Full Text View citing articles Show Details

87%

With polymethylhydrosiloxane; palladium on activated charcoal in ethanol

T=20°C;

Chandrasekhar; Reddy, Ch. Raji; Rao, R. Jagadeeshwar; Rao, J. Madhusudana

Synlett, 2002 , # 2 p. 349 - 351 Title/Abstract Full Text View citing articles Show Details

85%

With chloro-trimethyl-silane; sodium iodide; zinc in acetonitrile

T=55 - 60°C; 1 h;

Morita, Tsuyoshi; Kuroda, Koji; Okamoto, Yoshiki; Sakurai, Hiroshi

Chemistry Letters, 1981 , p. 921 - 924 Title/Abstract Full Text Show Details

Hide Details 85%

With indium; titanium tetrachloride in tetrahydrofuran

T=20°C; 0.0833333 h;

Yoo, Byung Woo; Choi, Kwang Hyun; Choi, Kyung Il; Kim, Joong Hyup

Synthetic Communications, 2003 , vol. 33, # 24 p. 4185 - 4189 Title/Abstract Full Text View citing articles Show Details

85%

With hexacarbonyl molybdenum in ethanol

1 h; Heating;

Yoo, Byung Woo; Choi, Jin Woo; Yoon, Cheol Min

Tetrahedron Letters, 2006 , vol. 47, # 1 p. 125 - 126 Title/Abstract Full Text View citing articles Show Details

85%

With [MoCl5]; sodium iodide in acetonitrile

T=20°C; 2.5 h;

Yoo, Byung Woo; Park, Min Chol

Synthetic Communications, 2008 , vol. 38, # 10 p. 1646 - 1650 Title/Abstract Full Text View citing articles Show Details

85%

With bismuth(III) chloride; indium in methanol

T=20°C; 1.5 h; Inert atmosphere; chemoselective reaction;

Yoo, Byung Woo; Choi, Jin Woo

Synthetic Communications, 2009 , vol. 39, # 19 p. 3550 - 3554 Title/Abstract Full Text View citing articles Show Details

78%

With triphenylphosphine; [MoO2Cl2(dmf)2] in tetrahydrofuran

3 h; Heating;

Sanz, Roberto; Escribano, Jaime; Fernandez, Yolanda; Aguado, Rafael; Pedrosa, Maria R.; Arnaiz, Francisco J.

Synlett, 2005 , # 9 art. no. D02405ST, p. 1389 - 1392 Title/Abstract Full Text View citing articles Show Details

69%

With indium; pivaloyl chloride in dichloromethane

T=20°C; 0.5 h;

Park, Eun Soo; Lee, Seung Hwan; Lee, Ji Hee; Rhee, Hak June; Yoon, Cheol Min

Synthesis, 2005 , # 20 art. no. F03405SS, p. 3499 - 3501 Title/Abstract Full Text View citing articles Show Details

48 %Chromat.

With carbon dioxide; water; iron

T=100°C; 10 h; AutoclaveGreen

Ma, Ran; Liu, An-Hua; Huang, Cheng-Bin; Li, Xue-Dong; He, Liang-Nian

Green Chemistry, 2013 , vol. 15, # 5 p. 1274 - 1279

chemistry; chemoselective reaction;

Title/Abstract Full Text View citing articles Show Details

With tetrahydroxydiboron in N,N-dimethylformamide

T=25°C; 0.2 h; Sealed tube; SolventTemperature;

Londregan, Allyn T.; Piotrowski, David W.; Xiao, Jun

Synlett, 2013 , vol. 24, # 20 art. no. ST-2013-S0695-L, p. 2695 - 2700 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1631299 Find similar reactions

A: 19% B: 2% C: 26% D: 12%

T=550°C;

Busby, Reginald E.; Hussain, Syed M.; Mohamed, Murtedza bin; Parrick, John; Shaw, C. J. Granville; et al.

Journal of Chemical Research, Miniprint, 1980 , # 12 p. 4935 - 4953 Title/Abstract Full Text Show Details

A: 19% B: 2% C: 26% D: 12%

T=550°C;

Busby, Reginald E.; Hussain, Syed M.; Mohamed, Murtedza bin; Parrick, John; Shaw, C. J. Granville; et al.

Journal of Chemical Research, Miniprint, 1980 , # 12 p. 4935 - 4953 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 1815977 Find similar reactions

ICR double resonance, proton affinity;

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Ellenberger, Mark R.; Dixon, David A.; Farneth, William E.

Journal of the American Chemical Society, 1981 , vol. 103, # 18 p. 5377 - 5382 Title/Abstract Full Text View citing articles Show Details

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96%

With titanium in tetrahydrofuran

0.25 h; Ambient temperature;

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Rx-ID: 2324528 Find similar reactions

Malinowski, Marek; Kaczmarek, Lukasz

Synthesis, 1987 , # 11 p. 1013 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 3889884 Find similar reactions

in acetonitrile

T=25°C; ΔG(excit.), ΔH(excit.), ΔS(excit.); Rate constantEquilibrium constantThermodynamic data;

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Arnett, Edward M.; Reich, Ronald

Journal of the American Chemical Society, 1980 , vol. 102, # 18 p. 5892 - 5902 Title/Abstract Full Text View citing articles Show Details

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17%

With 1,2-dichloro-ethane

7 h; Heating;

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Rx-ID: 4532039 Find similar reactions

Umemoto, Teruo; Tomizawa, Ginjiro; Hachisuka, Hitoharu; Kitano, Masakatsu

Journal of Fluorine Chemistry, 1996 , vol. 77, # 2 p. 161 - 168 Title/Abstract Full Text View citing articles Show Details

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96.5%

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With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride

T=160°C; 5 h; Hide Experimental Procedure

Rx-ID: 5255550 Find similar reactions

Wu, Jiang; Zhou, Junpeng; Shi, Yalei; Zhu, Jintao

Synthetic Communications, 2016 , vol. 46, # 19 p. 1619 - 1624 Title/Abstract Full Text Show Details

Syntheses of Compounds (a-g)

General procedure: A mixture of phenols (100.0 mmol) phenylphosphonic dichloride (11.0 mmol) and phosphorus pentachloride (110.0 mmol) was slowly heated to 160 °C while distilled the byproduct POCl3. And the mixture was stirred at the same temperature for 5 hours. TLC analysis showed the reaction had been finished. The POCl3 was evaporated in vacuum and the residue was poured into ice water, and it was neutralized with saturated aqueous sodium carbonate solution, and extracted with acetic ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, the obtained crude product was distilled or purified with silica gel chromatography, the target compound was obtained. The structures of compounds were confirmed by MS and 1H NMR data which were listed as follows.

90%

With pyridine; trichlorophosphate

T=180°C; P=150.015 - 900.09 Torr; 2 h; Neat (no solvent);

Sun, Zhihua; Wang, Han; Wen, Kun; Li, Ya; Fan, Erkang

Journal of Organic Chemistry, 2011 , vol. 76, # 10 p. 4149 - 4153 Title/Abstract Full Text View citing articles Show Details

43%

With N-chlorosuccinimide; triphenylphosphine in 1,4dioxane

Chlorination; substitution; 4 h; Heating;

Sugimoto, Osamu; Mori, Miho; Tanji, Ken-ichi

Tetrahedron Letters, 1999 , vol. 40, # 42 p. 7477 - 7478 Title/Abstract Full Text View citing articles Show Details

Hide Details

100 %Chromat.

With trichloroacetonitrile; triphenylphosphine in toluene

4 h; Reflux;

Kijrungphaiboon, Woranun; Chantarasriwong, Oraphin; Chavasiri, Wainthorn

Tetrahedron Letters, 2012 , vol. 53, # 6 p. 674 - 677 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5407339 Find similar reactions

Abramovitch; Tomasik

Journal of Heterocyclic Chemistry, 1975 , vol. 12, p. 501 Full Text Show Details

Boudakian et al.

Journal of Heterocyclic Chemistry, 1967 , vol. 4, p. 377,379 Full Text Show Details

Ishikawa

Nippon Kagaku Kaishi, 1941 , vol. 62, p. 1178,1180 Chem.Abstr., 1947 , # 5512 Full Text Show Details

Baker et al.

Chemistry and Industry (London, United Kingdom), 1969 , p. 1344

Full Text Show Details

Deutsche Gold und Silber-Scheideanstalt

Patent: DE2252002 , 1974 ; Chem.Abstr., vol. 81, # 25567 Full Text Show Details

Winkler; Fuerst

Chemische Technik (Leipzig, Germany), 1974 , vol. 26, # 4 p. 225 Chem.Abstr., vol. 81, # 25507f Full Text Show Details

Hoefling et al.

Patent: DD29611 , 1965 ; Chem.Abstr., 1965 , vol. 63, # 14824h Full Text Show Details

VEB Leuna-Werke

Patent: DE1200304 , 1963 ; Chem.Abstr., 1966 , vol. 64, # 5053 Full Text Show Details

VEB Leuna-Werke

Patent: FR1360438 , 1963 ; Chem.Abstr., 1964 , vol. 61, # 9472d Full Text Show Details

Bushby et al.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979 , p. 1578,1581 Full Text Show Details

VEB Leuna-Werke 'Walter Ulbricht'

Patent: GB958877 , 1963 ; Chem.Abstr., 1964 , vol. 61, # 8282d Full Text Show Details

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Syntex (U.S.A.) LLC

Patent: US2003/144303 A1, 2003 ; Title/Abstract Full Text Show Details

6.2:Step 2

Step 2 A mixture of tert-butyl 2,6-dichloro-4-pyridine carboxylate (1 g, 4.03 mmol) and isopropyl amine (3.4 ml, 40.3 mmol) in dry DMSO (5 mL) was heated, in a sealed tube, at 105° C. for 5 h. The mixture was cooled to room temperature and a solution of saturated ammonium chloride (30 ml) was added. The mixture was partitioned with EtOAc (40 mL) and the organic layer was collected and washed with an equal volume of brine. The aqueous phases were back extracted with EtOAc (2*30 ml), the organic phases combined, dried over MgSO4 and filtered. The crude material was loaded onto a flash silica gel column (EtOAc/hexanes 1:9) to provided the corresponding chloro pyridine (820 mg) as a light yellow semi-viscous oil. MS (ES+): 271.

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Eastman Kodak Company

Patent: US4916227 A1, 1990 ; Title/Abstract Full Text Show Details

Exemplary aryl halides contemplated for use in the practice of the present invention include: ... 2-chlorobenzyl ethyl ether, 2-bromobenzyl ethyl ether, 2-chlorothiophene, 2-bromothiophene, 2-chloropyridine, 2-bromopyridine, 2-chloro-3-methylnaphthalene, 2-bromo-3-methylnaphthalene, ... Hide Details

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Eastman Kodak Company

Patent: US4916227 A1, 1990 ; Title/Abstract Full Text Show Details

Examples of preferred monohalides which satisfy structural formula (I) include: 2-chlorotoluene, 2-chloropyridine, 4-fluoro-2-chlorotoluene, 2-chlorobenzyl methyl ether, 2-chlorobenzyl ethyl ether, 4-(N-ethyl-N-acetyl)-2-chlorotoluene, 6-(N-ethyl-N-acetyl)-2-chlorotoluene, 4-chlorotoluene,

4-chloroanisole, ...

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Eastman Kodak Company

Patent: US4916227 A1, 1990 ; Title/Abstract Full Text Show Details

The method according to claim 27 wherein said monohalide is selected from the group consisting of: 2-chlorotoluene, 2-chloropyridine, 4-fluoro-2-chlorotoluene, 2-chlorobenzyl methyl ether, 2-chlorobenzyl ethyl ether, 4-(N-ethyl-N-acetyl)-2-chlorotoluene, 6-(N-ethyl-N-acetyl)-2-chlorotoluene, 4-chlorotoluene, 4-chloroanisole, ...

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Adir, S.A.R.L.

Patent: US4613601 A1, 1986 ; Title/Abstract Full Text Show Details

The following compounds were prepared according to the methods given in Example 1: 2. 1-(benzodioxin-6-yl methyl)-4-(2-pyridyl)piperazine, M.P. of its dihydrochloride >250° C. with decomposition (anhydrous methanol), starting from: 6-chloromethyl benzodioxine and 1-(2-pyridyl)piperazine, or 2-chloropyridine and 1-(benzodioxin-6-yl)methyl)piperazine, or 6-formylbenzodioxine and 1-(2-pyridyl)piperazine.

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Griengl; Herfried; Foidl; Gabriele

Patent: US4304785 A1, 1981 ; Title/Abstract Full Text Show Details

2:EXAMPLE 2

EXAMPLE 2 5 g (1α, 2β, 3α)-1-ethyl-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2methyl-5-indanol ("diisoeugenol") are trickled, with agitation, into a solution of 13.4 g phosphoroxychloride in 20 m absolute pyridine and stirred for 12 hours at room temperature and for 3 hours at 70° C., then separated, after cooling, from the precipitated pyridinechloride, all volatile substances being carefully removed in vacuo and, finally dried for several hours over KOH.

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Olin Corporation

Patent: US4504667 A1, 1985 ; Title/Abstract Full Text Show Details

Comparison I

Comparison I A solution containing 2-chloropyridine and acetic acid was prepared in a glass flask. Then a 50percent by weight aqueous H2 O2 solution was added to the flask while keeping the reaction temperature below 50° C. with a water bath. The same procedure as used in Examples 1-10 was followed to obtain a 2-chloropyridine-N-oxide product except the reaction temperature was 70° C. instead of 80° C.

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Reilly Tar and Chemical Corporation

Patent: US4158093 A1, 1979 ; Title/Abstract Full Text Show Details

The process in claim 47 in which the selected quaternary salt or its acid salt is of a first pyridine base from the group consisting of 4-cyanopyridine; 2-methyl-4-cyanopyridine; 2-cyanopyridine; 2-chloropyridine.

With pyridine; N,N-diethylaniline

Hide Experimental Procedure

Merck Sharp and Dohme Corp.; Southern Research Institute; Arasappan, Ashok; Njoroge, F. George; Kwong, Cecil D.; Ananthan, Subramaniam; Bennett, Frank; Velazquez, Francisco; Girijavallabhan, Vinay M.; Huang, Yuhua; Kezar, III, Hollis S.; Maddry, Joseph A.; Reynolds, Robert C.; Roychowdhury, Abhijit; Fowler, Anita T.; Secrist, III, John A.; Kozlowski, Joseph A.; Shankar, Bandarpalle B.; Tong, Ling; Kim, Seong Heon; MacCoss, Malcolm; Venkatraman, Srikanth; Verma, Vishal

Patent: US9433621 B2, 2016 ; Title/Abstract Full Text Show Details

43.3:Procedure A-7

Step 3 A mixture of the pyridine (3304-3; 11.4 g) and diethylaniline (25 ml) in phosphorous oxychloride (228 ml) was heated to reflux for a period of 3 h. After cooling, the reaction mixture was added cautiously to ice water and the slurry was stirred for a period of 2.5 h. This mixture was extracted with EtOAc (*3) and the combined organic phases was washed with sat. aq. sodium bicarbonate, brine and dried (MgSO4). The volatiles were removed under reduced pressure. The residue was purified by silica gel column chromatography using EtOAc:hexanes (1:3) as eluent to give the chloropyridine (3304-4; 9.00 g).

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Rx-ID: 5407340 Find similar reactions

T=130°C;

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v. Pechmann; Baltzer

Chemische Berichte, 1891 , vol. 24, p. 3150 Full Text Show Details

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Rx-ID: 5407341 Find similar reactions

T=130 - 140°C;

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Fischer,O.

Chemische Berichte, 1898 , vol. 31, p. 611 Chemische Berichte, 1899 , vol. 32, p. 1298 Full Text Show Details

Rx-ID: 5407342

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Find similar reactions

T=140 - 150°C;

Fischer,O.

Chemische Berichte, 1899 , vol. 32, p. 1304 Full Text Show Details

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Rx-ID: 5407343 Find similar reactions

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Marckwald

Chemische Berichte, 1894 , vol. 27, p. 1323 Full Text Show Details

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With phosphorus pentachloride; trichlorophosphate

T=150 - 170°C;

Rx-ID: 5407344 Find similar reactions

Fischer,O.

Chemische Berichte, 1898 , vol. 31, p. 611 Chemische Berichte, 1899 , vol. 32, p. 1298 Full Text Show Details

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With phosphorus pentachloride; trichlorophosphate

Rx-ID: 5407345 Find similar reactions

Fischer,O.

Chemische Berichte, 1898 , vol. 31, p. 611

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T=150 - 170°C;

Chemische Berichte, 1899 , vol. 32, p. 1298 Full Text Show Details

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Rx-ID: 5407346 Find similar reactions

Gold- u. Silberscheideanst.

Patent: DE489183 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2638 Full Text Show Details

T=120°C;

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With phosphorus pentachloride; trichlorophosphate

Rx-ID: 5407347 Find similar reactions

Fischer,O.

Chemische Berichte, 1898 , vol. 31, p. 611 Chemische Berichte, 1899 , vol. 32, p. 1298 Full Text Show Details

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T=120°C;

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Rx-ID: 5407348 Find similar reactions

Gold- u. Silberscheideanst.

Patent: DE489183 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2638 Full Text Show Details

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90%

With chlorine in pyridine

T=0 - 5°C; 1 h;

Rx-ID: 5407349 Find similar reactions

Paraskewas, Spyridon

Synthesis, 1980 , # 5 p. 378 - 379 Title/Abstract Full Text Show Details

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With sulfuryl dichloride

T=120°C;

Rx-ID: 5676056 Find similar reactions

Bobranski et al.

Chemische Berichte, 1938 , vol. 71, p. 2385,2387 Full Text Show Details

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91.2%

With oxalyl dichloride; triethylamine in dichloromethane

T=5°C; 1 h; Temperature; Hide Experimental Procedure

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Rx-ID: 8862837 Find similar reactions

Anhui Guoxing Biochemical Co., Ltd.; Wang, Hongwei; Liang, Xichen; Zhou, Aimin; Wang, Zhangcai; Li, Wenbing; Zhao, Zhihua

Patent: CN105669535 A, 2016 ; Location in patent: Paragraph 0039; 0040 ; Title/Abstract Full Text Show Details

7:Example 7

95g of N-oxidopyridine was added to the flask, then add 190g of methylene chloride, 175 g of oxalyl chloride and 140g of triethylamine were stirred at condition of 5 deg.C and reacted for 1 hour; the reaction vessel was moved to the 500mL by distillation at a temperature carried out at 70 deg.C, the degree of vacuum distillation under reduced pressure 0.07Mpa condition, until after no liquid was distilled off, the temperature continues to rise to 90 deg.C, the degree of vacuum 0.09Mpa evaporated material is 2-chloropyridine. The remaining material is N- oxidized pyridine. After detecting the content of 2-chloropyridine was 95.6percent, yield 91.2percent.

90%

With triethylamine; trichlorophosphate in

Jung; Park

dichloromethane

T=40°C; 1 h;

Synthetic Communications, 2001 , vol. 31, # 16 p. 2507 - 2511 Title/Abstract Full Text View citing articles Show Details

With diisopropylamine; trichloromethyl chloroformate in dichloromethane

T=-40 - 20°C;

Narendar; Gangadasu; Ramesh, Ch.; Raju, B. China; Rao, V. Jayathirtha

Synthetic Communications, 2004 , vol. 34, # 6 p. 1097 - 1103 Title/Abstract Full Text View citing articles Show Details

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With copper(l) iodide; tetrabutyl ammonium fluoride; triphenylphosphine; bistriphenylphosphine-palladium(II) chloride; para-iodoanisole in N,N-dimethylformamide

T=20°C; 12 h;

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Rx-ID: 9962773 Find similar reactions

Pierrat, Philippe; Gros, Philippe; Fort, Yves

Organic Letters, 2005 , vol. 7, # 4 p. 697 - 700 Title/Abstract Full Text View citing articles Show Details

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With copper(l) iodide; tetrabutyl ammonium fluoride; triphenylphosphine; bistriphenylphosphine-palladium(II) chloride; para-iodoanisole in N,N-dimethylformamide

T=20°C; 12 h;

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Rx-ID: 9984285 Find similar reactions

Pierrat, Philippe; Gros, Philippe; Fort, Yves

Organic Letters, 2005 , vol. 7, # 4 p. 697 - 700 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9990507

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With copper(l) iodide; tetrabutyl ammonium fluoride; triphenylphosphine; bistriphenylphosphine-palladium(II) chloride; para-iodoanisole in N,N-dimethylformamide

T=20°C; 12 h;

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Pierrat, Philippe; Gros, Philippe; Fort, Yves

Organic Letters, 2005 , vol. 7, # 4 p. 697 - 700 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 10378365 Find similar reactions

B: 70%

With copper(l) iodide; zinc in ethanol

T=55 - 60°C; 3 h;

Singh, Sunil Kumar; Srinivasa Reddy; Mangle, Mangesh; Ravi Ganesh

Tetrahedron, 2007 , vol. 63, # 1 p. 126 - 130 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran 2.1: PPh3; CuI; TBAF / PdCl2(PPh3)2; 4iodoanisole / dimethylformamide / 12 h / 20 °C View Scheme

Rx-ID: 13000301 Find similar reactions

Pierrat, Philippe; Gros, Philippe; Fort, Yves

Organic Letters, 2005 , vol. 7, # 4 p. 697 - 700 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 23859820 Find similar reactions

Hamann, Lawrence G.; Kong, James; Edwards, James P.

Patent: US2003/149268 A1, 2003 ; Title/Abstract Full Text Show Details

3:EXAMPLE 3

EXAMPLE 3 (R/S)-8-Chloro-1,2,3,4-tetrahydro-2,2,4,10-tetramethyl-6-trifluoromethyl-9-pyrido[3,2-,]quinoline (Compound 103, Structure 2 of Scheme I, where R1=R3=R4=R5=Me, R2=R6=H). This compound was prepared from 1,2,3,4-tetrahydro-2,2,4,10-tetramethyl-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (0.127 g, 0.393 mmol) in the manner previously described for Compound 101 affording 125 mg (93percent) of the desired chloropyridine as a bright yellow solid. Data for Compound 103: 1H NMR (400 MHz, CDCl3) 7.75 (br s, 1H, 5-H), 7.28 (s, 1H, 7-H), 4.21 (br s, 1H, NH), 3.11 (ddq, 1H, J=12.9, 12.4, 6.3,4-H), 2.47 (s, 3H, 10-CH3), 1.84 and 1.53 [dd of ABq, 2H, JAB=13.0, JA=5.1, 1.6 (3-Heq), JB=12.9, 0 (3-Hax)], 1.47 (d, 3H, J=6.7, 4-CH3), 1.38 and 1.29 [2s, 2*3H, 2-(CH3)2]. A

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Rx-ID: 23859821 Find similar reactions

Hamann, Lawrence G.; Kong, James; Edwards, James P.

Patent: US2003/149268 A1, 2003 ; Title/Abstract Full Text Show Details

8:EXAMPLE 8

EXAMPLE 8 (R/S)-8-Chloro-4-ethyl-1,2,3,4-tetrahydro-6-trifluoromethyl-9-pyrido[3,2-g]quinoline (Compound 108, Structure 2 of Scheme I, where R1=R2=R3=R4=R6=H, R5=Et). This compound was prepared from 4-ethyl-1,2,3,4-tetrahydro-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (0.326 g, 1.11 mmol) in the manner previously described for Compound 101, affording 311 mg (90percent) of the desired chloropyridine as a bright yellow solid. Data for Compound 108: 1H NMR (400 MHz, CDCl3) 7.64 (br s, 1H, 5-H), 7.27 (s, 1H, 7-H) 6.93 (d, 11H, J=2.3, 10-H), 4.66 (br s, 1H, NH), 3.45 (m, 2H, 2-H), 2.87 (m, 1H, 4-H), 1.96 (m, 2H, 3-H), 1.70 (m, 2H, 4-CH2CH3), 1.02 (t, 3H, J=7.4, 4-CH2CH3). A

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Rx-ID: 23859822 Find similar reactions

Hamann, Lawrence G.; Kong, James; Edwards, James P.

Patent: US2003/149268 A1, 2003 ; Title/Abstract Full Text Show Details

9:EXAMPLE 9

EXAMPLE 9 (R/S)-8-Chloro-4-!ethyl-7-fluoro-1,2,3,4-tetrahydro-6-trifluoromethyl-9-pyrido[3,2-g]quinoline (Compound 109, Structure 2 of Scheme I. where R1=R2=R3=R4=H, R5=Et, R6=F).

This compound was prepared from 4-ethyl-7-fluoro-1,2,3,4-tetrahydro-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (0.326 g, 1.11 mmol) in the manner previously described for Compound 101, affording 311 mg (90percent) of the desired chloropyridine as a bright yellow solid. Data for Compound 109: 1H NMR (400 MHz, CDCl3) 7.68 (s, 11H, 5-H), 6.91 (s, 11H, 10-H), 4.62 (br s, 11H, NH), 3.46 (m,; 2H, 2-H), 2.87 (m, 1H, 4-H), 1.94 (m, 2H, 3-H), 1.69 (m, 2H, 4-CH2CH3), 1.02 (t, 3H, J=7.4,4-CH2CH3). A

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Rx-ID: 23859823 Find similar reactions

Hamann, Lawrence G.; Kong, James; Edwards, James P.

Patent: US2003/149268 A1, 2003 ; Title/Abstract Full Text Show Details

4:EXAMPLE 4

EXAMPLE 4 8-Chloro-1,2,3,4-tetrahydro-2,2-dimethyl-6-trifluoromethyl-9-pyrido[3,2-g]quinoline (Compound 104, Structure 2 of Scheme I, where R1=R2=R5=R6=H. R3=R4=Me). This compound was prepared from 1,2,3,4-tetrahydro-2,2-dimethyl-6-trifluoromethyl-8-pyrido[5,6-g]quinoline (4.00 g, 13.5 mmol) in the manner previously described for Compound 101 affording 3.99 g (94percent) of the desired chloropyridine as a bright yellow solid. Data for Compound 104: 1H NMR (400 MHz, CDCl3) 7.66 (s, 1H, 5-H), 7.25 (s, 1H, 7-H), 6.91 (s, 1H, 10-H), 4.43 (br s, 1H, NH), 3.00 (t, 2H, J=6.7, 4-H), 1.81 (t, 2H,J=6.7, 3-H), 1.31 [s, 6H, 2-(CH3)2]. A

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Rx-ID: 23859824 Find similar reactions

Hamann, Lawrence G.; Kong, James; Edwards, James P.

Patent: US2003/149268 A1, 2003 ; Title/Abstract Full Text Show Details

7:EXAMPLE 7

EXAMPLE 7 8-Chloro-7-fluoro-1,2,3,4-tetrahydro-2,2-dimethyl-6-trifluoromethyl-9-pyrido[3,2-g]quinoline (Compound 107, Structure 2 of Scheme I, where R1=R2=R5=H, R3=R4=Me, R6=F). This compound was prepared from 7-fluoro-1,2,3,4-tetrahydro-2,2-dimethyl-6-trifluoromethyl-8-pyridono[5,6-g]quinoline (0.302 g, 0.961 mmol) in the manner previously described for Compound 101, affording 310 mg (97percent) of the desired chloropyridine as a bright yellow solid. Data for Compound 107: 1H NMR (400 MHz, CDCl3) 7.69 (br s, 1H, 5-H), 6.89 (s, 1H, 10-H), 4.36 (br s, 1H, NH), 3.01 (dd, 2H, J=6.7, 6.6, 3-H), 1.80 (dd, 2H, J=6.7, 6.7, 2-H), 1.30 [s, 6H, 2-(CH3)2]. A

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Rx-ID: 24421879 Find similar reactions

With tert.-butyl lithium; Zinc chloride in tetrahydrofuran; pentane

Celltech Therapeutics Ltd.

Patent: US6114333 A1, 2000 ;

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Title/Abstract Full Text Show Details

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35.65:EXAMPLES 35-65

A solution of the protected bromopyridine (6.00 g, 17.50 mmol) in anhydrous THF (150 ml) was cooled to -100° (liquid nitrogen-diethyl ether) then treated dropwise with tert-butyllithium (22.0 ml of a 1.7M solution in pentane, 37.40 mmol) and the resulting thick yellow mixture stirred at -100° for 30 min. Zinc chloride (35.2 ml of a 0.5M solution in THF, 17.60 mmol) was slowly added and the mixture stirred at -75° for 30 min then allowed to warm to room temperature whereupon 2,4-dichloropyrimidine (3.98 g, 26.71 mmol) and tetrakis(triphenylphosphine)-palladium(o) (1.00 g, 0.86 mmol) were added. The resulting mixture was refluxed for 5 h then allowed to cool to room temperature. Saturated aqueous ammonium chloride was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with brine then dried (MgSO4) and evaporated to give a crude product which was purified by recrystallisation (ethyl acetate-hexane) to afford the desired chloropyridine (3.03 g) as a beige solid m.p. 182-183°. δH (CDCl3) 1.48 (9H, s), 3.56 (4H, m), 3.69 (4H, m), 6.68 (1H, d, J 9.0 Hz), 7.49 (1H, d, J 5.4 Hz), 8.24 (1H, dd, J 2.5, 9.0 Hz), 8.49 (1H, d, J 5.4 Hz) and 8.82 (1H, d, J 2.5 Hz).

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82%

With chlorine in chloroform; water; acetic acid

T=15 - 17°C; 0.5 h;

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Rx-ID: 25927768 Find similar reactions

Maslankiewicz, Andrzej; Marciniec, Krzysztof; Pawlowski, Maciej; Zajdel, Pawel

Heterocycles, 2007 , vol. 71, # 9 p. 1975 - 1990 Title/Abstract Full Text View citing articles Show Details

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97 %Spectr.

With acetic acid; silver carbonate in dimethyl sulfoxide

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Rx-ID: 29041489 Find similar reactions

Lu, Pengfel; Sanchez, Carolina; Cornella, Josep; Larrosa, Igor

Organic Letters, 2009 , vol. 11, # 24 p. 5710 - 5713

T=140°C; 16 h;

Title/Abstract Full Text View citing articles Show Details

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91 %Spectr.

With acetic acid; silver carbonate in dimethyl sulfoxide

T=140°C; 16 h;

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Rx-ID: 29041490 Find similar reactions

Lu, Pengfel; Sanchez, Carolina; Cornella, Josep; Larrosa, Igor

Organic Letters, 2009 , vol. 11, # 24 p. 5710 - 5713 Title/Abstract Full Text View citing articles Show Details

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92%

With trans-[Cu(gly)2]*(H2O); anhydrous tetramethylammonium chloride in ethanol

T=100°C; Finkelstein Reaction; 12 h; Schlenk techniqueInert atmosphere; Hide Experimental Procedure

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Rx-ID: 34020502 Find similar reactions

Verma, Sanny; Saran, Sandeep; Jain, Suman L.

Applied Catalysis A: General, 2014 , vol. 472, p. 178 - 183 Title/Abstract Full Text View citing articles Show Details

General procedure for aryl and heteroaryl bromide–chloride exchange reaction

General procedure: A Schlenk tube was charged with catalyst 1 (10 mol percent), aryl (or heteroaryl) bromide (1.0 mmol), tetramethylammonium chloride (Me4NCl) (2.0 mmol), and EtOH (2.0 mL) under nitrogen atmosphere. The Schlenk tube was sealed with a Teflon valve, and then the reaction mixture was stirred at 100 °C for a period as mentioned in Table 2 (the reaction progress was monitored by GC analysis). After completion of the reaction, the solvent was removed under reduced pressure. The residue obtained was purified via silica gel chromatography (eluent: petroleum ether/ethyl acetate = 10/1) to afford aryl chlorides. The yield of the products was determined by high resolution GC–MS analysis and the identity of the products was confirmed by comparing their physical and spectral data with the known compounds.

93 %Chromat.

With copper(I) oxide; anhydrous tetramethylammonium chloride; L-proline in ethanol

T=110°C; 20 h; Inert atmosphere;

Feng, Xiujuan; Qu, Yiping; Han, Yanlei; Yu, Xiaoqiang; Bao, Ming; Yamamoto, Yoshinori

Chemical Communications, 2012 , vol. 48, # 76 p. 9468 - 9470 Title/Abstract Full Text View citing articles Show Details

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97 %Spectr.

With potassium trimethylsilonate in d7-N,Ndimethylformamide

T=70°C; 48 h; Temperature;

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Rx-ID: 42783227 Find similar reactions

Kuboviov, Lenka; Bürglov, Kristna; Hlav, Jan

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 21 p. 4824 - 4828 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1530737 Find similar reactions

70%

Stage #1: With 2,2,6,6tetramethylpiperidinyl-lithium in tetrahydrofuran

T=-78°C; 1.5 h; Stage #2: With diclazuril; water-d2 in tetrahydrofuran

T=-78°C; 1 h; Further stages.;

Gros, Philippe; Choppin, Sabine; Mathieu, Julien; Fort, Yves

Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 234 - 237 Title/Abstract Full Text View citing articles Show Details

With nbutyllithium; diclazuril; iodobenzene; waterd2; diisopropylamine

1.) THF, -40 deg C, 2.) -70 deg C, 15 min.; Yield given. Multistep reaction;

Mallet, Marc

Journal of Organometallic Chemistry, 1991 , vol. 406, # 1+2 p. 49 - 56 Title/Abstract Full Text View citing articles Show Details

With nbutyllithium; diclazuril; diisopropylamine

1) THF, hexane, 0 deg C, 3 h 2) D2O, -70 deg C, 1 h; Yield given. Multistep reaction;

Trecourt, Francois; Marsais, Francis; Guengoer, Timur; Queguiner, Guy

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 9 p. 2409 - 2415 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With n-butyllithium; N,N,N',N,tetramethylethylenediamine

Stage #2: With water-d2

Elmore, Charles S.; Landvatter, Scott; Dorff, Peter N.; Powell, Mark E.; Killick, David; Blake, Timothy; Hall, James; Heys, J. Richard; Harding, John; Urbanek, Rebecca; Ernst, Glen

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 342 - 349 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8544095 Find similar reactions

100%

Stage #1: With n-butyllithium; BuLiLiDMAE in hexane

T=-78°C; Metallation; 1 h; Stage #2: With methanol-d1 in tetrahydrofuran

T=-78 - 0°C; Condensation; 1 h;

Choppin, Sabine; Gros, Philippe; Fort, Yves

Organic Letters, 2000 , vol. 2, # 6 p. 803 - 805 Title/Abstract Full Text View citing articles Show Details

65%

Stage #1: With n-butyllithium; 2(dimethylamino)-ethanol in hexane

T=-78°C; 1 h; Stage #2: With diclazuril; water-d2 in hexane

T=-78°C; 0.25 h; Further stages.;

Gros, Philippe; Choppin, Sabine; Mathieu, Julien; Fort, Yves

Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 234 - 237 Title/Abstract Full Text View citing articles Show Details

33%

Stage #1: With n-butyllithium; 2(dimethylamino)-ethanol in hexane

T=-78°C; 1 h; Inert atmosphere; Stage #2: With methanol-d1 in hexane

T=-78 - 0°C; 0.666667 h; Inert atmosphere; regioselective reaction;

Carlsson, Anna-Carin C.; Graefenstein, Juergen; Budnjo, Adnan; Laurila, Jesse L.; Bergquist, Jonas; Karim, Alavi; Kleinmaier, Roland; Brath, Ulrika; Erdelyi, Mate

Journal of the American Chemical Society, 2012 , vol. 134, # 12 p. 5706 - 5715 Title/Abstract Full Text View citing articles Show Details

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With (tricyclohexylphosphine)(1,5cyclooctadiene)pyridineiridium(I) hexafluorophosphate; rhodium; deuterium in tetrahydrofuran; dichloromethane

T=20°C; 4 h;

Schou, Soren Christian

Journal of Labelled Compounds and Radiopharmaceuticals, 2010 , vol. 53, # 5-6 p. 375 - 381 Title/Abstract Full Text View citing articles Show Details

Schou, Soren Christian

Journal of Labelled Compounds and Radiopharmaceuticals, 2009 , vol. 52, # 9 p. 376 - 381 Title/Abstract Full Text View citing articles Show Details

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100 %Spectr.

With Ag2CO3; water-d2 in dimethyl sulfoxide T=140°C; 16 h; Inert atmosphere; chemoselective reaction;

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Rx-ID: 33135998 Find similar reactions

Grainger, Rachel; Nikmal, Arif; Cornella, Josep; Larrosa, Igor

Organic and Biomolecular Chemistry, 2012 , vol. 10, # 16 p. 3172 - 3174 Title/Abstract Full Text View citing articles Show Details

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49%

Stage #1: With n-butyllithium in diethyl

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Rx-ID: 36240819 Find similar reactions

Nielsen, Daniel K.; Huang, Chung-Yang; Doyle, Abigail G.

ether; hexane

T=-78°C; 1 h; Schlenk techniqueInert atmosphere; Stage #2: With water-d2 in diethyl ether; hexane

T=23°C; Schlenk techniqueInert atmosphere;

Journal of the American Chemical Society, 2013 , vol. 135, # 36 p. 13605 - 13609 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1504402 Find similar reactions

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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28%

With trichlorophosphate

T=120°C; 3 h;

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Rx-ID: 25964571 Find similar reactions

Pavlik, James W.; Laohhasurayotin, Somchoke

Journal of Heterocyclic Chemistry, 2007 , vol. 44, # 6 p. 1485 - 1492 Title/Abstract Full Text View citing articles Show Details

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With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1504782 Find similar reactions

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, not above -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1505087 Find similar reactions

A: 70% B: 15%

With dichloromethane

Ambient temperature;

Hebel, David; Rozen, Shlomo

Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6298 - 6301 Title/Abstract Full Text View citing articles Show Details

A: 70% B: 15%

With dichloromethane

Ambient temperature;

Hebel, David; Rozen, Shlomo

Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6298 - 6301 Title/Abstract Full Text View citing articles Show Details

A: 70% B: 15%

in dichloromethane

Ambient temperatureother N-heterocycles, other solvents; Mechanism;

Hebel, David; Rozen, Shlomo

Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6298 - 6301 Title/Abstract Full Text View citing articles Show Details

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A: 70% B: 15%

With dichloromethane; AcOF in monofluorotrichloromethane

Ambient temperaturevar. halogenomethanes or primary alcohols; other substituted pyridines; Product distributionMechanism;

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Hebel, David; Rozen, Shlomo

Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1123 - 1125 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 11158135 Find similar reactions

A: 14 % Spectr. B: 15 % Spectr. C: 71 % Spectr.

With chloroform-d1

T=24°C; Title compound not separated from byproducts.;

Song, Fenhong; St. Hilaire, Valentine R.; White, Emil H.

Organic Letters, 1999 , vol. 1, # 12 p. 1957 - 1959 Title/Abstract Full Text View citing articles Show Details

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With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1506009 Find similar reactions

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 22302 Find similar reactions

With chlorine

T=270 - 300°C; Leiten ueber Bimsstein;

Wibaut; Nicolai

Recueil des Travaux Chimiques des Pays-Bas, 1939 , vol. 58, p. 709,721 Full Text Show Details

With steam; chlorine

T=350°C; Leiten ueber Siliciumcarbid;

Olin Mathieson Chem. Corp.

Patent: US2820791 , 1956 ;

With chlorine

T=350 - 420°C; Leiten ueber Bimsstein;

Wibaut; Nicolai

Recueil des Travaux Chimiques des Pays-Bas, 1939 , vol. 58, p. 709,721 Full Text Show Details

Full Text Show Details

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A: 3 % Chromat. B: 1 % Chromat. C: 2.5 % Chromat. D: 72 % Chromat.

With triethylamine

0.0833333 h; Ambient temperature;

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Umemoto, Teruo; Tomizawa, Ginjiro

Journal of Organic Chemistry, 1989 , vol. 54, # 7 p. 1726 - 1731 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5410649 Find similar reactions

T=270 - 300°C;

Wibaut; Nicolai

Recueil des Travaux Chimiques des Pays-Bas, 1939 , vol. 58, p. 709,721 Full Text Show Details

T=350 - 420°C;

Wibaut; Nicolai

Recueil des Travaux Chimiques des Pays-Bas, 1939 , vol. 58, p. 709,721 Full Text Show Details

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Rx-ID: 5410880 Find similar reactions

Steinhaeuser; Diepolder

Journal fuer Praktische Chemie (Leipzig), 1916 , vol. <2> 93, p. 395 Full Text Show Details

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With phosphorus pentachloride; trichlorophosphate

T=200°C;

Rx-ID: 5410881 Find similar reactions

Steinhaeuser; Diepolder

Journal fuer Praktische Chemie (Leipzig), 1916 , vol. <2> 93, p. 395 Full Text Show Details

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Synthesize Find similar Rx-ID: 10387255 Find similar reactions

B: 75%

With copper(l) iodide; zinc in ethanol

T=55 - 60°C; 3 h;

Singh, Sunil Kumar; Srinivasa Reddy; Mangle, Mangesh; Ravi Ganesh

Tetrahedron, 2007 , vol. 63, # 1 p. 126 - 130 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28120145 Find similar reactions

B: 35%

Stage #1: pyridine With chlorine; di-tert-butyl peroxide in tetrachloromethane; water

T=231 - 244°C; 0.00361111 - 0.00722222 h; Stage #2: tertiary butyl peroxybenzenoate Product distribution / selectivity;

Reilly Industries, Inc.

Patent: US6369231 B1, 2002 ; Location in patent: Page column 4-5 ; Title/Abstract Full Text Show Details

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91%

With titanium tetrachloride; tin(ll) chloride in diethyl ether

0.5 h; Ambient temperature;

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Rx-ID: 2324529 Find similar reactions

Balicki, Roman; Kaczmarek, Lukasz; Malinowski, Marek

Synthetic Communications, 1989 , vol. 19, # 5and6 p. 897 - 900 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 34794594 Find similar reactions

A: 80 %Chromat. B: 20 %Chromat.

With indium; [N-butylthiazolium][Br]

T=95°C; 14 h; Green chemistry;

Canete, Alvaro F.; Salas, Cristian O.; Zacconi, Flavia C.

Molecules, 2013 , vol. 18, # 1 p. 398 - 407 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1504735 Find similar reactions

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

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Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1531130 Find similar reactions

A: 19%

in dichloromethane

15 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 5591209 Find similar reactions

Kursanow; Ignat'ewa

Zhurnal Obshchei Khimii, 1943 , vol. 13, p. 62,65 Chem.Abstr., 1944 , p. 356 Full Text Show Details

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in solid partially decompd. at room temp.;

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Jona, E.; Jamnicky, M.

Journal of Thermal Analysis, 1983 , vol. 27, p. 359 - 366 Full Text View citing articles Show Details

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With CsSO4F in chloroform

4 h; Ambient temperature; Product distribution;

Stavber, Stojan; Zupan, Marko

Tetrahedron Letters, 1990 , vol. 31, # 5 p. 775 - 776 Title/Abstract Full Text View citing articles Show Details

With CsSO4F in chloroform

Ambient temperature0.5-4 h; Yield given. Yields of byproduct given;

Stavber, Stojan; Zupan, Marko

Tetrahedron Letters, 1990 , vol. 31, # 5 p. 775 - 776 Title/Abstract Full Text View citing articles Show Details

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A: 20% B: 78%

With 1,3-Dichloro-5,5-dimethyl-2,4imidazolidinedione; acetic acid in dichloromethane; water

T=0 - 20°C; Inert atmosphere;

Pu, Yu-Ming; Christesen, Alan; Ku, Yi-Yin

Tetrahedron Letters, 2010 , vol. 51, # 2 p. 418 - 421 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1506014 Find similar reactions

B: 61%

With tetrabutyl ammonium fluoride; fluorine

multistep reaction; other trimethylsilyl derivatives; Mechanism;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 5421684 Find similar reactions

A: 9% B: 62% C: 4.5%

With chlorine in cyclohexane

T=75°C; 1 h;

Paraskewas, Spyridon

Synthesis, 1980 , # 5 p. 378 - 379 Title/Abstract Full Text Show Details

A: 9% B: 62% C: 4.5%

With chlorine in cyclohexane

T=75°C; 1 h;

Paraskewas, Spyridon

Synthesis, 1980 , # 5 p. 378 - 379 Title/Abstract Full Text Show Details

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Rx-ID: 1531125 Find similar reactions

A: 4.7%

in dichloromethane

6 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

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Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 1531128 Find similar reactions

A: 12%

in dichloromethane

15 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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With tetrabutyl ammonium fluoride; fluorine

1.) CH2Cl2, not above -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

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Kiselyov, Alexander S.; Strekowski, Lucjan

Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4476 - 4478 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1575725 Find similar reactions

With EtOD

1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; a new "homotransmetalation" reaction, further reagents and conditions; Product distributionMechanism;

Mallet, M.; Queguiner, G.

Tetrahedron, 1985 , vol. 41, # 16 p. 3433 - 3440 Title/Abstract Full Text View citing articles Show Details

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A: 58% B: 40%

Stage #1: With tert.-butyl lithium in tetrahydrofuran

T=-78°C; 0.0833333 h; Stage #2: With water-d2 in tetrahydrofuran

T=-78°C;

Pierrat, Philippe; Gros, Philippe; Fort, Yves

Synlett, 2004 , # 13 p. 2319 - 2322 Title/Abstract Full Text View citing articles Show Details

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B: 1.5 g (57.5%)

With phosphorus pentachloride in chloroform; water

Merck and Co., Inc.

Patent: US5308854 A1, 1994 ;

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Title/Abstract Full Text Show Details

8.A:Step A

Step A Preparation of 2-chloro-5-ethyl-6-methyl-3-nitropyridine A mixture of 5-ethyl-6-methyl-3-nitro-2-(1H)-pyridinone (2.38 g, 13 mmol) and phosphorus pentachloride (3.3 g, 15.6 mmol) was heated under an atmosphere of nitrogen at 140°-150° C. for 15 minutes. The resultant brown oil was then treated with water and the product extracted into chloroform. The organic extract was washed three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (15 torr). The residue was passed through a small plug of silica gel, eluted with 2percent methanol in chloroform. Collection and concentration of appropriate fractions yielded 1.5 g (57.5percent) of the corresponding chloropyridine as a clear pale brown oil. A

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Rx-ID: 25458041 Find similar reactions

B: 1.5 g (57.5%)

in chloroform; water

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MERCK and CO. INC.

Patent: EP462808 A2, 1991 ; Title/Abstract Full Text Show Details

8.A:Step A

Step A : Preparation of 2-chloro-5-ethyl-6-methyl-3-nitropyridine A mixture of 5-ethyl-6-methyl-3-nitro-2-(1H)-pyridinone (2.38 g, 13 mmol) and phosphorus penta-chloride (3.3 g, 15.6 mmol) was heated under an atmosphere of nitrogen at 140-150°C for 15 minutes. The resultant brown oil was then treated with water and the product extracted into chloroform. The organic extract was washed three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (15 torr). The residue was passed through a small plug of silica gel, eluted with 2percent methanol in chloroform. Collection and concentration of appropriate fractions yielded 1.5 g (57.5percent) of the corresponding chloropyridine as a clear pale brown oil. A

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Rx-ID: 9762055 Find similar reactions

A: 11% B: 60%

Stage #1: pyridine With fluorine in dichloromethane

T=-78 - -50°C; Stage #2: tert-butylisonitrile in

Kiselyov, Alexander S.

Tetrahedron Letters, 2005 , vol. 46, # 13 p. 2279 - 2282 Title/Abstract Full Text View citing articles Show Details

dichloromethane

T=-50 - 0°C; 4 h;

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Rx-ID: 9762058 Find similar reactions

A: 12% B: 64%

Stage #1: pyridine With fluorine in dichloromethane

T=-78 - -50°C; Stage #2: n-butyl isocyanide in dichloromethane

T=-50 - 0°C; 4 h;

Kiselyov, Alexander S.

Tetrahedron Letters, 2005 , vol. 46, # 13 p. 2279 - 2282 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1815978 Find similar reactions

T=34.9°C; ΔG0; Thermodynamic data;

Mishima, Masaaki; Ariga, Toshifumi; Tsuno, Yuho; Ikenaga, Kazutoshi; Kikukawa, Kiyoshi

Chemistry Letters, 1992 , # 3 p. 489 - 492 Title/Abstract Full Text Show Details

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A: 14%

in dichloromethane

10 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 1531106 Find similar reactions

A: 18%

in dichloromethane

12 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 1531132 Find similar reactions

A: 3.4% B: 11.6%

in dichloromethane

3 h; Ambient temperatureIrradiation;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 1531135 Find similar reactions

A: 3.8%

in dichloromethane

3 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given;

Terashima, Masanao; Seki, Koh-ichi; Yoshida, Chihiro; Ohkura, Kazue; Kanaoka, Yuichi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 3 p. 1009 - 1015 Title/Abstract Full Text Show Details

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Rx-ID: 9762056 Find similar reactions

A: 24% B: 55%

Stage #1: pyridine With fluorine in dichloromethane

T=-78 - -50°C; Stage #2: phenyl isocyanate in dichloromethane

T=-50 - 0°C; 4 h;

Kiselyov, Alexander S.

Tetrahedron Letters, 2005 , vol. 46, # 13 p. 2279 - 2282 Title/Abstract Full Text View citing articles Show Details

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A: 25 % Chromat. B: 9 % Chromat. C: 7 % Chromat. D: 5 % Chromat.

With dichloromethane; sodium methylate

0.166667 h; Ambient temperature;

Unemoto, Teruo; Tomizawa, Ginjiro

Tetrahedron Letters, 1987 , vol. 28, # 24 p. 2705 - 2708 Title/Abstract Full Text View citing articles Show Details

A: 25 % Chromat. B: 9 % Chromat. C: 7 % Chromat. D: 5 % Chromat.

With sodium methylate in dichloromethane

0.166667 h; Ambient temperature;

Unemoto, Teruo; Tomizawa, Ginjiro

Tetrahedron Letters, 1987 , vol. 28, # 24 p. 2705 - 2708 Title/Abstract Full Text View citing articles Show Details

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A: 63 % Chromat. B: 1 % Chromat. C: 22 % Chromat. D: 6 % Chromat.

With dichloromethane; diethylamine

0.0833333 h; Ambient temperature;

Unemoto, Teruo; Tomizawa, Ginjiro

Tetrahedron Letters, 1987 , vol. 28, # 24 p. 2705 - 2708 Title/Abstract Full Text View citing articles Show Details

A: 63 % Chromat. B: 1 % Chromat. C: 22 % Chromat. D: 6 % Chromat.

With diethylamine in dichloromethane

0.0833333 h; Ambient temperature;

Unemoto, Teruo; Tomizawa, Ginjiro

Tetrahedron Letters, 1987 , vol. 28, # 24 p. 2705 - 2708 Title/Abstract Full Text View citing articles Show Details