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O
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30 reactions in Reaxys
2018-05-11 16h:56m:25s (UTC)
O
Search as: Product, As drawn, No mixtures ) AND (IDE.XRN=1868308))
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1/11
2018-05-11 16:57:29
N
O O
O O
Rx-ID: 3342818 View in Reaxys 1/30 Yield 88 %
Conditions & References General procedure for the synthesis of 6, 9 and 15 General procedure: A solution of 5 (1 g,6.33 mmol) in dry DMF (5 mL) was cooled to 0 C, and POCl3(2 mL, 21.43 mmol) was added drop-wise. After being stirred at0 C for an hour, the mixture was heated at 95 C for 4 h. The reactionwas quenched with ice-cold water, extracted with ethyl acetate(20 mL 2) and washed with water. Organic phase was driedwith anhydrous Na2SO4 and concentrated in-vacuo to get a residue.The residue was purified by flash column chromatography (ethylacetate-hexane) to get 6 as creamy solid (1.04 g, 88percent): mp 80–81 C; IR (KBr) mmax 3019, 2929, 1673, 1607, 1579, 1487, 1384;1H NMR (CDCl3, 300 MHz) d 4.00 (s, 3H), 7.22–7.25 (t, J = 9.0 Hz,1H), 7.39–7.43 (t, J = 6.0 Hz, 1H), 7.59–7.68 (m, 2H), 8.00–8.03 (d,J = 9.0 Hz, 1H), 9.27–9.30 (d, J = 9.0 Hz, 1H), 10.81 (s, 1H); 13CNMR (CDCl3, 75 MHz) d 56.9, 112.9, 116.9, 125.1, 125.3, 128.6,128.9, 130.2, 131.9, 137.9, 164.3, 192.3. Electrospray mass (MeOH)for C12H10O3: 187.1 [M+H]+, 209.2 [M+Na]+, 225.2 [M+K]+. With trichlorophosphate, Time= 5h, Vilsmeier-Haack Formylation Kumar, Balagani Sathish; Ravi, Kusumoori; Verma, Amit Kumar; Fatima, Kaneez; Hasanain, Mohammad; Singh, Arjun; Sarkar, Jayanta; Luqman, Suaib; Chanda, Debabrata; Negi, Arvind S.; Bioorganic and Medicinal Chemistry; vol. 25; nb. 4; (2017); p. 1364 - 1373 View in Reaxys
84 %
With bis(trichloromethyl) carbonate in tetrachloromethane, Time= 2h, T= 40 - 50 °C , Vilsmeier-Haack formylation Shan; Shi; Su; Organic Preparations and Procedures International; vol. 36; nb. 4; (2004); p. 337 - 340 View in Reaxys
75 %
Stage 1: With trichlorophosphate in 1,2-dichloro-ethane, Time= 8h, T= 0 °C , Inert atmosphere, Reflux Stage 2: With water in 1,2-dichloro-ethane, Inert atmosphere, Cooling with ice Zhang, Sheng; Wang, Yi; Feng, Xiujuan; Bao, Ming; Journal of the American Chemical Society; vol. 134; nb. 12; (2012); p. 5492 - 5495 View in Reaxys With sodium hydroxide, pyrophosphoryl chloride, 1) 100 deg C, 28 h, Yield given. Multistep reaction Downie, Ian M.; Earle, Martyn J.; Heaney, Harry; Shuhaibar, Khamis F.; Tetrahedron; vol. 49; nb. 19; (1993); p. 4015 4034 View in Reaxys
O HO
O
Rx-ID: 44972646 View in Reaxys 2/30 Yield
Conditions & References Reaction Steps: 2 1: potassium carbonate / acetone / 1 h / Heating 2: trichlorophosphate / 5 h With potassium carbonate, trichlorophosphate in acetone, 2: |Vilsmeier-Haack Formylation Kumar, Balagani Sathish; Ravi, Kusumoori; Verma, Amit Kumar; Fatima, Kaneez; Hasanain, Mohammad; Singh, Arjun; Sarkar, Jayanta; Luqman, Suaib; Chanda, Debabrata; Negi, Arvind S.; Bioorganic and Medicinal Chemistry; vol. 25; nb. 4; (2017); p. 1364 - 1373 View in Reaxys
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2/11
2018-05-11 16:57:29
I
HO
O
O
O
Rx-ID: 784997 View in Reaxys 3/30 Yield 87 %
Conditions & References With potassium carbonate in N,N-dimethyl-formamide, Time= 20h, T= 45 °C Basak, Tymoteusz; Grudzień, Krzysztof; Barbasiewicz, Michał; European Journal of Inorganic Chemistry; vol. 2016; nb. 21; (2016); p. 3513 - 3523 View in Reaxys With alcoholic alkali, T= 120 °C , in geschlossenem Gefaess Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys Helbronner; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 44; Bulletin de la Societe Chimique de France; vol. <3> 29; (1903); p. 880 View in Reaxys Synthesis and Characterization of the OrganicDyad (E)-3-(2-methoxynaphthalen-1-yl)-1-(4-methoxyphenyl)Prop-2-en-1One (MNTMA) To a solution of 2-hydroxynapthaldehyde 1 (3.0 g,17.4 mmol) in anhydrous acetone (30 mL) was addedanhydrous K2CO3 (2.97 g, 21.5 mmol) and methyliodide(5.43 g, 38.2 mmol) and the resulting mixture was heatedto 45 C (bath temperature) under argon for 2 hours. Aftercompletion of the reaction (monitored by TLC), the solventwas removed in vacuo and the residue worked up inthe usual way using ethyl acetate and water to yield thecrude 2-methoxynapthaldehyde (3.0 gm). The crude 2 wasused for the next step without further purification. With potassium carbonate in acetone, Time= 2h, T= 45 °C , Inert atmosphere Dutta, Gopa; Paul, Abhijit; Yadav, Somnath; Bardhan, Munmun; De, Asish; Chowdhury, Joydeep; Jana, Aindrila; Ganguly, Tapan; Journal of Nanoscience and Nanotechnology; vol. 15; nb. 8; (2015); p. 5775 - 5784; Art.No: A44 View in Reaxys
HO
I
O
O
OH
O
Rx-ID: 43321804 View in Reaxys 4/30 Yield 95 %
Conditions & References 53.a : Preparation of 2-methoxy-1-naphthaldehyde Reaction flask was added 9.0 g (48. Ommol) 3-hydroxy-2-naphthoic acid, 8.3 g (60mmol) of anhydrous potassium carbonate and 30 ml of DMF dry, stirred, ice-bath cooling, 7 . 5 g (52. 5mmol) of methyl iodide was slowly added dropwise to the reaction flask And heated to 90 ° C for 6 hours. The reaction mixture was poured into water, extracted with methylene chloride, washed three times with a saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and evaporated to dryness to give a yellow solid 8.5 g, yield 95percent With potassium carbonate in N,N-dimethyl-formamide, Time= 10h, T= 90 °C , Cooling with ice Patent; INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF MEDICAL SCIENCES; YANG, GUANGZHONG; QIN, FANG; ZHANG, JIANJUN; WANG, YAFANG; WEN, HUI; JI, CHENGXUE; (38 pag.); CN101602750; (2016); (B) Chinese View in Reaxys
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3/11
2018-05-11 16:57:29
O
O
HO
O
Rx-ID: 39370278 View in Reaxys 5/30 Yield
Conditions & References With pyridinium chlorochromate in dichloromethane, T= 20 °C Mimori, Seisuke; Koshikawa, Yukari; Mashima, Yu; Mitsunaga, Katsuyoshi; Kawada, Koichi; Kaneko, Masayuki; Okuma, Yasunobu; Nomura, Yasuyuki; Murakami, Yasuoki; Kanzaki, Tetsuto; Hamana, Hiroshi; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 4; (2015); p. 811 - 814 View in Reaxys
O
O
Rx-ID: 7024567 View in Reaxys 6/30 Yield
Conditions & References Bergman; Tetrahedron Letters; (1972); p. 4723 View in Reaxys Rieche et al.; Chemische Berichte; vol. 93; (1960); p. 88,90 View in Reaxys Wolter; Kosler; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 10; (1970); p. 401,402 View in Reaxys A few illustrative examples of preferred aldehydes include ... 2-hydroxy-5-methoxybenzaldehyde 2-hydroxy-1-naphthaldehyde 5-iodovanillin isophthalaldehyde 2-methoxy-1-naphthaldehyde 4-methoxy-1-naphthaldehyde 3-methyl-p-anisaldehyde 10-methylanthracene-9-carboxaldehyde ... Patent; Ethyl Corporation; US4837327; (1989); (A) English View in Reaxys 10 Patent; GENMEDICA THERAPEUTICS SL; UNIVERSIDAD DE BARCELONA; WO2006/3189; (2006); (A1) English View in Reaxys 7 Patent; GENMEDICA THERAPEUTICS; WO2006/61140; (2006); (A2) English View in Reaxys 10 Patent; Exposito, Miriam Royo; Clauzel, Luc Marti; Martin, Anna Abella; Vicente, Silvia Garcia; Yinbert, Xavier Testar; Olarte, Antonio Zorzano; Prieto, Manuel Palacin; Palomera, Fernando Albericio; Font, Francesc Yraola; Mian, Alec; US2007/66682; (2007); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/11
2018-05-11 16:57:29
O
O O
O
O O
O
Rx-ID: 9555231 View in Reaxys 7/30 Yield
Conditions & References
92 %
With zirconium(IV) chloride in methanol, Time= 0.0833333h, T= 20 °C Smitha; Reddy, Ch. Sanjeeva; Tetrahedron; vol. 59; nb. 48; (2003); p. 9571 - 9576 View in Reaxys
N
O O
O
O
Rx-ID: 759935 View in Reaxys 8/30 Yield
Conditions & References
70 %
With trichlorophosphate in 1,2-dichloro-benzene, Time= 1h, T= 100 °C , Vilsmeier formylation Matsubara, Hiroshi; Yasuda, Shinji; Sugiyama, Hiroyuki; Ryu, Ilhyong; Fujii, Yasuyuki; Kita, Katsumi; Tetrahedron; vol. 58; nb. 20; (2002); p. 4071 - 4076 View in Reaxys With trichlorophosphate Narasimhan,N.S.; Mali,R.S.; Tetrahedron; vol. 31; (1975); p. 1005 - 1009 View in Reaxys Reid,D.H.; Sutherland,R.G.; Journal of the Chemical Society; (1963); p. 3295 - 3308 View in Reaxys Fuson; Chadwick; Journal of Organic Chemistry; vol. 13; (1948); p. 484,485 View in Reaxys
Cl
Cl
Br
O
Cl O
O
Rx-ID: 4765599 View in Reaxys 9/30 Yield
Conditions & References
50 %
With 1,10-phenanthroline hydrate, iron, copper, copper(I) bromide in N,N-dimethyl-formamide, Time= 72h, T= 60 °C Leonel; Paugam; Nedelec; Journal of Organic Chemistry; vol. 62; nb. 20; (1997); p. 7061 - 7064 View in Reaxys
O
O S
O
O
HO
O
O
O
Rx-ID: 757048 View in Reaxys 10/30
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/11
2018-05-11 16:57:29
Yield
Conditions & References
80 %
With sodium hydride in N,N-dimethyl-formamide, Time= 6h, Ambient temperature Kral, Andreas; Laatsch, Hartmut; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 48; nb. 10; (1993); p. 1401 1407 View in Reaxys With potassium hydroxide Barger; Starling; Journal of the Chemical Society; vol. 99; (1911); p. 2032 View in Reaxys Kazitsyna,L.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 31; (1961); p. 313 - 323,286 - 294 View in Reaxys S
2H
2H
–O
O
O
O
2H
O
Rx-ID: 1973731 View in Reaxys 11/30 Yield
Conditions & References in d(4)-methanol, var. reagent conc., Rate constant Kice, John L.; Lotey, Harvinder; Journal of Organic Chemistry; vol. 54; nb. 15; (1989); p. 3596 - 3602 View in Reaxys
HO
OH
O O
O
O O
Rx-ID: 3957719 View in Reaxys 12/30 Yield
Conditions & References
33 %
With manganese triacetate in acetic acid, Time= 0.0166667h, Heating Nishino, Hiroshi; Tsunoda, Katsunori; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 545 - 550 View in Reaxys
HO
OH
O O
O
O
O O
HO
O
Rx-ID: 3957720 View in Reaxys 13/30 Yield 25 %, 8 %
Conditions & References With manganese triacetate in acetic acid, Time= 0.0166667h, Heating Nishino, Hiroshi; Tsunoda, Katsunori; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 545 - 550 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/11
2018-05-11 16:57:29
carbamate ammonium
O
HO
O
Rx-ID: 18175220 View in Reaxys 14/30 Yield
Conditions & References Reaction Steps: 2 2: 33 percent / manganese(III) acetate / acetic acid / 0.02 h / Heating With manganese triacetate in acetic acid Nishino, Hiroshi; Tsunoda, Katsunori; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 545 - 550 View in Reaxys Reaction Steps: 2 2: 25 percent / manganese(III) acetate / acetic acid / 0.02 h / Heating With manganese triacetate in acetic acid Nishino, Hiroshi; Tsunoda, Katsunori; Kurosawa, Kazu; Bulletin of the Chemical Society of Japan; vol. 62; nb. 2; (1989); p. 545 - 550 View in Reaxys
O
O O
O O
O
O
O
Rx-ID: 2118284 View in Reaxys 15/30 Yield
Conditions & References
98 %
With oxygen, 5,15,10,20-tetraphenylporphyrin in tetrachloromethane, Time= 1h, T= 5 °C , Irradiation Matsumoto, Masakatsu; Kuroda, Keiko; Suzuki, Yoshito; Tetrahedron Letters; vol. 22; nb. 34; (1981); p. 3253 - 3256 View in Reaxys
O
O
O O
O
O
O
O
Rx-ID: 2653390 View in Reaxys 16/30 Yield 40 %, 46 %
Conditions & References With oxygen, 5,15,10,20-tetraphenylporphyrin in tetrachloromethane, Time= 1h, T= 5 °C , Irradiation Matsumoto, Masakatsu; Kuroda, Keiko; Suzuki, Yoshito; Tetrahedron Letters; vol. 22; nb. 34; (1981); p. 3253 - 3256 View in Reaxys
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7/11
2018-05-11 16:57:29
O O
O N
F
O
N
F
O F
F
F
F
Rx-ID: 3779749 View in Reaxys 17/30 Yield
Conditions & References
67 %
Bergman, Jan; Renstroem, Lars; Sjoeberg, Birger; Tetrahedron; vol. 36; (1980); p. 2505 - 2512 View in Reaxys
O
O O
Rx-ID: 20673418 View in Reaxys 18/30 Yield
Conditions & References Reaction Steps: 2 1: 94 percent / acetonitrile / 2 h / Heating 2: 67 percent in acetonitrile Bergman, Jan; Renstroem, Lars; Sjoeberg, Birger; Tetrahedron; vol. 36; (1980); p. 2505 - 2512 View in Reaxys Reaction Steps: 3 1: CS2; AlCl3 / Zersetzung des Produktes mit Wasser 2: aqueous NaOH-solution 3: bei der Zersetzung des entstehenden 2-Methoxy-naphthaldehyd-(1)-anils mit 25prozentiger Schwefelsaeure With carbon disulfide, sodium hydroxide, aluminium trichloride Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys S
O
O
O
O
Rx-ID: 1125822 View in Reaxys 19/30 Yield
Conditions & References With triphenylphosphine in benzene Strating,J. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 86; (1967); p. 641 - 649 View in Reaxys
Cl
S
Cl
O
O O
Rx-ID: 1005025 View in Reaxys 20/30
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/11
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Yield
Conditions & References (i) TiCl4, CH2Cl2, (ii) aq. HCl, Multistep reaction Gross,H.; Matthey,G.; Chemische Berichte; vol. 97; (1964); p. 2606 - 2613 View in Reaxys
O O
Cl OH Cl
O
Cl
Rx-ID: 489816 View in Reaxys 21/30 Yield
Conditions & References With potassium hydroxide Broquet-Borgel; Annales de Chimie (Cachan, France); vol. <13> 3; (1958); p. 204,248 View in Reaxys
O
O
Mg Br
O
Rx-ID: 22105143 View in Reaxys 22/30 Yield
Conditions & References Reaction Steps: 2 1: THF 2: aqueous KOH With tetrahydrofuran, potassium hydroxide Broquet-Borgel; Annales de Chimie (Cachan, France); vol. <13> 3; (1958); p. 204,248 View in Reaxys
zinc cyanide
O
O O
Rx-ID: 7024569 View in Reaxys 23/30 Yield
Conditions & References With hydrogenchloride, aluminium trichloride, potassium chloride, Reagens 4:Aether; und Erhitzen des Reaktionsprodukts mit Wasser Acharya; Shah; Wheeler; Journal of the Chemical Society; (1940); p. 817 View in Reaxys With hydrogenchloride, aluminium trichloride, benzene, und Zersetzen des entstandenen Imidhydrochlorids mit Salzsaeure Adams; Montgomery; Journal of the American Chemical Society; vol. 46; (1924); p. 1521 View in Reaxys
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9/11
2018-05-11 16:57:29
OH
O
acid
N H
O
N O
O
Rx-ID: 7980402 View in Reaxys 24/30 Yield
Conditions & References Brady; Goldstein; Journal of the Chemical Society; (1927); p. 1961 View in Reaxys
O
O S
Na +
–O
O
O
O
O
O
Rx-ID: 750125 View in Reaxys 25/30 Yield
Conditions & References T= 115 - 120 °C Mundici; Gazzetta Chimica Italiana; vol. 39 II; (1909); p. 125 View in Reaxys
O
O
sodium salt of 2-oxy-naphthaldehyde-(1)
S O
O
O
O
Rx-ID: 7024568 View in Reaxys 26/30 Yield
Conditions & References With toluene, T= 115 - 120 °C Mundici; Gazzetta Chimica Italiana; vol. 39 II; (1909); p. 126 View in Reaxys
N O
O O
Rx-ID: 194466 View in Reaxys 27/30 Yield
Conditions & References With hydrogenchloride, aluminium trichloride, benzene, zuletzt bei 45grad, und Zersetzung des entstandenen salzsauren Imids durch Erhitzen mit Wasser Gattermann; Justus Liebigs Annalen der Chemie; vol. 357; (1907); p. 373 View in Reaxys
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10/11
2018-05-11 16:57:29
I
alcoholic alkali
HO
O
O
O
Rx-ID: 5806390 View in Reaxys 28/30 Yield
Conditions & References T= 120 °C Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys Helbronner; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 44; Bulletin de la Societe Chimique de France; vol. <3> 29; (1903); p. 880 View in Reaxys
O
H 2N O
O O O
OH
Rx-ID: 710811 View in Reaxys 29/30 Yield
Conditions & References bei der Zersetzung des entstehenden 2-Methoxy-naphthaldehyd-(1)-anils mit 25prozentiger Schwefelsaeure Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys
O O O O
O
O
Rx-ID: 22135027 View in Reaxys 30/30 Yield
Conditions & References Reaction Steps: 2 1: aqueous NaOH-solution 2: bei der Zersetzung des entstehenden 2-Methoxy-naphthaldehyd-(1)-anils mit 25prozentiger Schwefelsaeure With sodium hydroxide Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 309 View in Reaxys
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11/11
2018-05-11 16:57:29