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12 reactions in Reaxys
2016-05-27 13h:04m:28s (EST)
O NH 2
1. Query I O
Search as: As drawn
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F
F
O
F
O
HN
O
I H 2N O
I O
Rx-ID: 28933737 View in Reaxys 1/12 Yield
Conditions & References
97 %
With sodium hydroxide in methanol, Time= 2h, T= 40 °C , Inert atmosphere Trachsel, Daniel; Nichols, David E.; Kidd, Stephanie; Hadorn, Marcel; Baumberger, Franz; Chemistry and Biodiversity; vol. 6; nb. 5; (2009); p. 692 - 704 View in Reaxys H
H 13C
13C
13
C
O
13C
O
I
13
C
13C
HCl
O
H
H C
13 13C 13C
13C
13C
O
13C
HCl
H
H 2N
H 2N
Rx-ID: 38014847 View in Reaxys 2/12 Yield
Conditions & References
48 %
Stage 1: With iodine, silver sulphate in ethanol, Time= 48h, Inert atmosphere Stage 2: With hydrogenchloride in diethyl ether, isopropyl alcohol, pH= 4 Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys 2H
O
2H
2H
2H
I
2H
O
O N
2H 2H
2H
NH 2
I
O
O 2H
O 2H
2H
2H
Rx-ID: 11289591 View in Reaxys 3/12 Yield
Conditions & References With hydrazine hydrate in isopropyl alcohol, Time= 1.5h, T= 100 °C Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys
O
O
O I
I H 2N
N O
O
O
Rx-ID: 11289592 View in Reaxys 4/12 Yield
Conditions & References With hydrazine hydrate in isopropyl alcohol, Time= 1.5h, T= 100 °C Xu, Ya-Zhu; Chen, Chinpiao; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 13; (2006); p. 1187 - 1200 View in Reaxys
Copyright © 2016 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.
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I
H 13C 13CH O
13C
13CH
O
H 13C 13CH
H
13
C
13C
13C
13
C H
13
C
O
13C
HCl
H 2N
Rx-ID: 38014762 View in Reaxys 5/12 Yield
Conditions & References Reaction Steps: 7 1.1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 2.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 3.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 4.1: ammonium acetate / 2 h / 70 °C 5.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 6.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 6.2: pH 3 7.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 7.2: pH 4 With sodium tetrahydroborate, N-bromosuccinmide, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, iodine, titanium tetrachloride, silver sulphate, ethyl acetate in methanol, ethanol, dichloromethane, chloroform, ethyl acetate, N,N-dimethyl-formamide, 3.1: |Rieche Formylation / 4.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
H 13C 13CH HO 13C
13CH
H 13C 13CH
I
H
13
C
13C
13
O
C
13
C
O
13 13C
C
HCl
H H 2N
Rx-ID: 38014784 View in Reaxys 6/12 Yield
Conditions & References Reaction Steps: 8 1.1: sodium hydroxide / water / 0.5 h / |Inert atmosphere 1.2: 1 h / 0 - 50 °C / |Inert atmosphere 2.1: N-bromosuccinmide / chloroform; N,N-dimethyl-formamide / 70 °C 3.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 4.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 5.1: ammonium acetate / 2 h / 70 °C 6.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 7.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 7.2: pH 3 8.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 8.2: pH 4 With sodium tetrahydroborate, N-bromosuccinmide, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, iodine, titanium tetrachloride, silver sulphate, ethyl acetate, sodium hydroxide in methanol, ethanol, dichloromethane, chloroform, water, ethyl acetate, N,N-dimethyl-formamide, 4.1: |Rieche Formylation / 5.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
Copyright © 2016 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.
3/5
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H
H 13C 13C
Br
13C
13C
I
O
13C 13CH
O
H
H
13
C
13C
13C
13
C H
13
C
O
13C
HCl
H 2N
Rx-ID: 38014793 View in Reaxys 7/12 Yield
Conditions & References Reaction Steps: 6 1.1: copper(l) iodide; ethyl acetate / N,N-dimethyl-formamide; methanol / 48 h / 80 °C / |Sealed tube; |Inert atmosphere 2.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 3.1: ammonium acetate / 2 h / 70 °C 4.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 5.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 5.2: pH 3 6.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 6.2: pH 4 With sodium tetrahydroborate, copper(l) iodide, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, iodine, titanium tetrachloride, silver sulphate, ethyl acetate in methanol, ethanol, dichloromethane, ethyl acetate, N,N-dimethyl-formamide, 2.1: |Rieche Formylation / 3.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
H C
13
H 13C O
13C
13C
I
O
13C
H
13
C
13C
13
13CH
O
C
13
C
O
13 13C
C
HCl
H
H
H 2N
Rx-ID: 38014830 View in Reaxys 8/12 Yield
Conditions & References Reaction Steps: 5 1.1: titanium tetrachloride / dichloromethane / 17 h / -5 - 4 °C / |Inert atmosphere 2.1: ammonium acetate / 2 h / 70 °C 3.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 4.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 4.2: pH 3 5.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 5.2: pH 4 With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, iodine, titanium tetrachloride, silver sulphate in methanol, ethanol, dichloromethane, ethyl acetate, 1.1: |Rieche Formylation / 2.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
H
H 13C O
13C
13C
13C
H
13C 13C
I
O O
O
H
13C 13C
13C
13C
13C 13C
O HCl
H
H 2N
Rx-ID: 38014835 View in Reaxys 9/12 Yield
Conditions & References Reaction Steps: 4 1.1: ammonium acetate / 2 h / 70 °C 2.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 3.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 3.2: pH 3 4.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere
Copyright © 2016 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.
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4.2: pH 4 With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, ammonium acetate, hydrogen, iodine, silver sulphate in methanol, ethanol, ethyl acetate, 1.1: |Henry Nitro Aldol Condensation Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H C
13
H 13C 13
O
C
O
13
C
I
13 13
C H O
C O
H
13C 13C
13C
13C
13C
O
13C
HCl
H
N
H 2N
O
Rx-ID: 38014842 View in Reaxys 10/12 Yield
Conditions & References Reaction Steps: 3 1.1: sodium tetrahydroborate; ethanol / ethyl acetate / 1 h / 22 °C 2.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 2.2: pH 3 3.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 3.2: pH 4 With sodium tetrahydroborate, ethanol, palladium 10 on activated carbon, hydrogen, iodine, silver sulphate in methanol, ethanol, ethyl acetate Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys H
H 13C O
13C
13C
13C
H O
O
13C
I
13C
H
13
C
13C
13
O
N
C
13
C
O
13 13C
C
HCl
H H 2N
O
Rx-ID: 38014845 View in Reaxys 11/12 Yield
Conditions & References Reaction Steps: 2 1.1: hydrogen; palladium 10 on activated carbon / methanol / 4 h 1.2: pH 3 2.1: iodine; silver sulphate / ethanol / 48 h / |Inert atmosphere 2.2: pH 4 With palladium 10 on activated carbon, hydrogen, iodine, silver sulphate in methanol, ethanol Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 57; nb. 5; (2014); p. 378 - 387 View in Reaxys
O I H 2N O
Rx-ID: 7736963 View in Reaxys 12/12 Yield
Conditions & References Phthalimid 2a, Hydrazinhydrat Braun et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 1543 View in Reaxys
Copyright © 2016 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.
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