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Date
26 reactions in Reaxys
2016-06-10 04h:59m:53s (EST)
26 reactions in Reaxys
2016-06-10 05h:00m:14s (EST)
NH 2
1. Query
O
O
Search as: As drawn 2. Query
(1. Query) AND itemno in (2)
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O H 2N
OH
H
NH 2
H
O O
Rx-ID: 20710106 View in Reaxys 1/26 Yield
Conditions & References Reaction Steps: 6 3: Heating 5: 1) BuLi / 1) THF, -78 deg C; 2) THF 6: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 6 3: Heating 5: 1) BuLi / 1) THF, -78 deg C; 2) THF 6: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 6 3: Heating 5: 1) BuLi / 1) THF, -78 deg C; 2) THF 6: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 6 3: Heating 5: 1) BuLi / 1) THF, -78 deg C; 2) THF 6: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 6 1: tetrahydrofuran 2: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 3: xylene / 36 h / Heating 4: 94 percent / CH2Cl2 / 72 h / Ambient temperature 5: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 20 h 6: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 6 1: tetrahydrofuran 2: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 3: xylene / 36 h / Heating 4: 94 percent / CH2Cl2 / 72 h / Ambient temperature 5: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 12 h 6: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10
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With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 6 1: tetrahydrofuran 2: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 3: xylene / 36 h / Heating 4: 94 percent / CH2Cl2 / 72 h / Ambient temperature 5: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 6: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 6 1: tetrahydrofuran 2: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 3: xylene / 36 h / Heating 4: 94 percent / CH2Cl2 / 72 h / Ambient temperature 5: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 10 h 6: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 6 1: tetrahydrofuran 2: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 3: xylene / 36 h / Heating 4: 94 percent / CH2Cl2 / 72 h / Ambient temperature 5: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 6: 1.) 0.25 aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys 6 :[0604] The solution of compound 3E-1 (3 g, 22.8 mmol) in 30 mL of MeOH/HCl was heated at 40°C for 20h. The solvent was removed under reduced pressure. The residual was diluted with water, neutralized with saturated aqueous NaHC03, extracted with EtOAc (100 mLx3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residual was used directly for the next step (2.5 g, crude yield 76percent). 1H NMR (400 MHz, CDC13): δ 3.68 (s, 3H), 3.14 (s, 1H), 0.94 (s, 9H). With hydrogenchloride in methanol, Time= 20h, T= 40 °C Patent; INTERMUNE, INC.; BUCKMAN, Brad; NICHOLAS, John, B.; SEREBRYANY, Vladimir; SEIWERT, Scott, D.; WO2012/40242; (2012); (A1) English View in Reaxys
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O
H
N
O
NH 2 O
N
O
O
O
H 2N
Rx-ID: 3071555 View in Reaxys 2/26 Yield
Conditions & References
84 %
With trifluoroacetic acid in tetrahydrofuran, Time= 4h, Ambient temperature Groth, Ulrich; Halfbrodt, Wolfgang; Schoellkopf, Ulrich; Liebigs Annalen der Chemie; nb. 4; (1992); p. 351 - 356 View in Reaxys With trifluoroacetic acid in tetrahydrofuran, Time= 4h, Ambient temperature, Yields of byproduct given Groth, Ulrich; Halfbrodt, Wolfgang; Schoellkopf, Ulrich; Liebigs Annalen der Chemie; nb. 4; (1992); p. 351 - 356 View in Reaxys
N
H
NH 2 O
N H
O
Rx-ID: 20482639 View in Reaxys 3/26 Yield
Conditions & References Reaction Steps: 4 1: 77 percent / conc. sulfuric acid / 48 h / Ambient temperature 2: 96 percent / H2 / 10percent Pd/C / aq. ethanol / 2280 Torr 3: 76 percent / conc. HCl / 100 °C 4: 52 percent / HCl gas / Heating With hydrogenchloride, sulfuric acid, hydrogen, palladium on activated charcoal in ethanol Speelman, Johanna C.; Talma, Auke G.; Kellogg, Richard M.; Meetsma, A.; Boer, J. L. de; et al.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1055 - 1062 View in Reaxys
H 2N
O
H
NH 2 O
N H
O
Rx-ID: 20484018 View in Reaxys 4/26 Yield
Conditions & References Reaction Steps: 3 1: 96 percent / H2 / 10percent Pd/C / aq. ethanol / 2280 Torr 2: 76 percent / conc. HCl / 100 °C 3: 52 percent / HCl gas / Heating With hydrogenchloride, hydrogen, palladium on activated charcoal in ethanol Speelman, Johanna C.; Talma, Auke G.; Kellogg, Richard M.; Meetsma, A.; Boer, J. L. de; et al.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1055 - 1062 View in Reaxys
H
NH 2
O
O O
Rx-ID: 20487178 View in Reaxys 5/26 Yield
Conditions & References Reaction Steps: 5
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1: 82 percent / methanol / 20 h / Ambient temperature 2: 77 percent / conc. sulfuric acid / 48 h / Ambient temperature 3: 96 percent / H2 / 10percent Pd/C / aq. ethanol / 2280 Torr 4: 76 percent / conc. HCl / 100 °C 5: 52 percent / HCl gas / Heating With hydrogenchloride, sulfuric acid, hydrogen, palladium on activated charcoal in methanol, ethanol Speelman, Johanna C.; Talma, Auke G.; Kellogg, Richard M.; Meetsma, A.; Boer, J. L. de; et al.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1055 - 1062 View in Reaxys
O
H
O O
O HN
NH 2 O O
Rx-ID: 39424843 View in Reaxys 6/26 Yield
Conditions & References With trifluoroacetic acid in dichloromethane, Time= 1h, T= 20 °C , Inert atmosphere Yamada, Takeshi; Hirose, Tomoyasu; OA mura, Satoshi; Sunazuka, Toshiaki; European Journal of Organic Chemistry; vol. 2015; nb. 2; (2015); p. 296 - 301 View in Reaxys
O
O
H
O
NH 2 O
N H
O
O
Rx-ID: 9331375 View in Reaxys 7/26 Yield
Conditions & References With hydrogen, palladium on activated charcoal in methanol Davies, Stephen J.; Ayscough, Andrew P.; Beckett, R. Paul; Clements, John M.; Doel, Sheila; Pratt, Lisa M.; Spavold, Zoe M.; Thomas, S. Wayne; Whittaker, Mark; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 16; (2003); p. 2715 - 2718 View in Reaxys
HO H
O
O
NH
H
NH 2
O
O O
Rx-ID: 14212345 View in Reaxys 8/26 Yield
Conditions & References Reaction Steps: 2 1: CH2Cl2 2: H2 / Pd/C / methanol With hydrogen, palladium on activated charcoal in methanol, dichloromethane Davies, Stephen J.; Ayscough, Andrew P.; Beckett, R. Paul; Clements, John M.; Doel, Sheila; Pratt, Lisa M.; Spavold, Zoe M.; Thomas, S. Wayne; Whittaker, Mark; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 16; (2003); p. 2715 - 2718 View in Reaxys
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O H
NH
NH 2 O
HN O
O
Rx-ID: 20718577 View in Reaxys 9/26 Yield
Conditions & References Reaction Steps: 3 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 3 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 3 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 3 2: 1) BuLi / 1) THF, -78 deg C; 2) THF 3: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 3 1: 94 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 20 h 3: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 3 1: 94 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 12 h 3: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 3 1: 94 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 3: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864
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View in Reaxys Reaction Steps: 3 1: 94 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 10 h 3: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 3 1: 94 percent / CH2Cl2 / 72 h / Ambient temperature 2: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 3: 1.) 0.25 aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O H 2N
H N
O O
H
NH 2 O
H
O
Rx-ID: 20718665 View in Reaxys 10/26 Yield
Conditions & References Reaction Steps: 4 1: Heating 3: 1) BuLi / 1) THF, -78 deg C; 2) THF 4: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 4 1: Heating 3: 1) BuLi / 1) THF, -78 deg C; 2) THF 4: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 4 1: Heating 3: 1) BuLi / 1) THF, -78 deg C; 2) THF 4: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 4 1: Heating 3: 1) BuLi / 1) THF, -78 deg C; 2) THF 4: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
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Reaction Steps: 4 1: xylene / 36 h / Heating 2: 94 percent / CH2Cl2 / 72 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 20 h 4: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 4 1: xylene / 36 h / Heating 2: 94 percent / CH2Cl2 / 72 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 12 h 4: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 4 1: xylene / 36 h / Heating 2: 94 percent / CH2Cl2 / 72 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 4: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 4 1: xylene / 36 h / Heating 2: 94 percent / CH2Cl2 / 72 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 10 h 4: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 4 1: xylene / 36 h / Heating 2: 94 percent / CH2Cl2 / 72 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 4: 1.) 0.25 aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium in dichloromethane, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O
H
H
NH 2 O
O HN O
O
Rx-ID: 20720592 View in Reaxys 11/26 Yield
Conditions & References Reaction Steps: 5 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium
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Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 5 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 5 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 5 2: Heating 4: 1) BuLi / 1) THF, -78 deg C; 2) THF 5: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 5 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 2: xylene / 36 h / Heating 3: 94 percent / CH2Cl2 / 72 h / Ambient temperature 4: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 20 h 5: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 5 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 2: xylene / 36 h / Heating 3: 94 percent / CH2Cl2 / 72 h / Ambient temperature 4: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 12 h 5: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 5 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 2: xylene / 36 h / Heating 3: 94 percent / CH2Cl2 / 72 h / Ambient temperature 4: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 5: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864
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View in Reaxys Reaction Steps: 5 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 2: xylene / 36 h / Heating 3: 94 percent / CH2Cl2 / 72 h / Ambient temperature 4: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 10 h 5: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 5 1: triethylamine / tetrahydrofuran; CHCl3 / 1.) -70 deg C, 8 h, 2.) room temp., 2 h 2: xylene / 36 h / Heating 3: 94 percent / CH2Cl2 / 72 h / Ambient temperature 4: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 5: 1.) 0.25 aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, dichloromethane, chloroform, xylene Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O
H
N
NH 2 O
N
O
O
Rx-ID: 20349356 View in Reaxys 12/26 Yield
Conditions & References Reaction Steps: 4 1: 1) n-BuLi / 1) hexane, THF, -70 deg C, 15 min, 2) 4 h 2: 62 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -70 °C 3: 99 percent / potassium azodicarboxylate, AcOH / methanol / 1 h / Ambient temperature 4: 0.1 N TFA / tetrahydrofuran / 4 h / Ambient temperature With n-butyllithium, potassium diazodicarboxylate, acetic acid, trifluoroacetic acid in tetrahydrofuran, methanol, hexane Groth, Ulrich; Halfbrodt, Wolfgang; Schoellkopf, Ulrich; Liebigs Annalen der Chemie; nb. 4; (1992); p. 351 - 356 View in Reaxys Reaction Steps: 2 1: 1) BuLi / 1) THF, -78 deg C; 2) THF 2: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 2 1: 1) BuLi / 1) THF, -78 deg C; 2) THF 2: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 2 1: 1) BuLi / 1) THF, -78 deg C; 2) THF 2: 0.25N aq. HCl / Ambient temperature
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With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 2 1: 1) BuLi / 1) THF, -78 deg C; 2) THF 2: 0.25N aq. HCl / Ambient temperature With hydrogenchloride, n-butyllithium Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 20 h 2: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 12 h 2: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 2: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 10 h 2: 1.) 0.25 N aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys Reaction Steps: 2 1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) -70 deg C, 8 h 2: 1.) 0.25 aq. HCl, 2.) conc. aq. NH3 / 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10 With hydrogenchloride, ammonium hydroxide, n-butyllithium Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O
HO
H 2N
OH
H
NH 2
H
O O
Rx-ID: 1593662 View in Reaxys 13/26 Yield 52 %
Conditions & References With hydrogenchloride, Heating Speelman, Johanna C.; Talma, Auke G.; Kellogg, Richard M.; Meetsma, A.; Boer, J. L. de; et al.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1055 - 1062
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View in Reaxys
O HO
H
HN
NH 2
H
O
O O
O
Rx-ID: 39424837 View in Reaxys 14/26 Yield
Conditions & References Reaction Steps: 2 1: methanol / dichloromethane; diethyl ether / 0.5 h / 20 °C / |Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / |Inert atmosphere With methanol, trifluoroacetic acid in diethyl ether, dichloromethane Yamada, Takeshi; Hirose, Tomoyasu; OA mura, Satoshi; Sunazuka, Toshiaki; European Journal of Organic Chemistry; vol. 2015; nb. 2; (2015); p. 296 - 301 View in Reaxys
O
H
N
NH 2 O
N
O
O
Rx-ID: 20358151 View in Reaxys 15/26 Yield
Conditions & References Reaction Steps: 2 1: 99 percent / potassium azodicarboxylate, AcOH / methanol / 1 h / Ambient temperature 2: 0.1 N TFA / tetrahydrofuran / 4 h / Ambient temperature With potassium diazodicarboxylate, acetic acid, trifluoroacetic acid in tetrahydrofuran, methanol Groth, Ulrich; Halfbrodt, Wolfgang; Schoellkopf, Ulrich; Liebigs Annalen der Chemie; nb. 4; (1992); p. 351 - 356 View in Reaxys
O
N
H N
NH 2 O
O
E
O
Cl
Rx-ID: 20358921 View in Reaxys 16/26 Yield
Conditions & References Reaction Steps: 3 1: 62 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -70 °C 2: 99 percent / potassium azodicarboxylate, AcOH / methanol / 1 h / Ambient temperature 3: 0.1 N TFA / tetrahydrofuran / 4 h / Ambient temperature With n-butyllithium, potassium diazodicarboxylate, acetic acid, trifluoroacetic acid in tetrahydrofuran, methanol, hexane Groth, Ulrich; Halfbrodt, Wolfgang; Schoellkopf, Ulrich; Liebigs Annalen der Chemie; nb. 4; (1992); p. 351 - 356 View in Reaxys
H
H 2N
NH 2 O
O NH 2
O
Rx-ID: 20497246 View in Reaxys 17/26
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Yield
Conditions & References Reaction Steps: 2 1: 76 percent / conc. HCl / 100 °C 2: 52 percent / HCl gas / Heating With hydrogenchloride Speelman, Johanna C.; Talma, Auke G.; Kellogg, Richard M.; Meetsma, A.; Boer, J. L. de; et al.; Journal of Organic Chemistry; vol. 54; nb. 5; (1989); p. 1055 - 1062 View in Reaxys
O
O
N
H
O N
O
NH 2
O
H
NH 2
O
Rx-ID: 2555714 View in Reaxys 18/26 Yield
Conditions & References With hydrogenchloride, ammonium hydroxide, 1.) room temp., 12 h, 2.) H2O, ether, pH=8-10, Yield given. Multistep reaction. Title compound not separated from byproducts Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys With hydrogenchloride, Ambient temperature Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
O
O
N
H
O
N
O
NH 2 H
O
NH 2
O
Rx-ID: 2555715 View in Reaxys 19/26 Yield
Conditions & References With hydrogenchloride, ammonium hydroxide, 1.) room temp., 3 h, 2.) H2O, ether, pH=8-10, Yield given. Multistep reaction Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys With hydrogenchloride, Ambient temperature Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
O
O
N
N
O
H
NH 2
O
H
NH 2
O O
Rx-ID: 2566785 View in Reaxys 20/26 Yield
Conditions & References With hydrogenchloride, ammonium hydroxide, 1.) room temp., 48 h, 2.) H2O, ether, pH=8-10, Yield given. Multistep reaction
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Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys With hydrogenchloride, Ambient temperature Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
O
N
H N
NH 2
O
O
O
O
H
NH 2
O
O H N
H
H 2N
O
O H
Rx-ID: 2573728 View in Reaxys 21/26 Yield
Conditions & References
5%
With hydrogenchloride, ammonium hydroxide, 1.) room temp., 20 h, 2.) H2O, ether, pH=8-10, Yield given. Multistep reaction Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O
N
O
H N O
O
O
NH 2
H H
O
O
O
H N H 2N
O
O
O
NH 2
O O H
O O
Rx-ID: 2585671 View in Reaxys 22/26 Yield
Conditions & References
5%
With hydrogenchloride, ammonium hydroxide, 1.) room temp., 6 h, 2.) H2O, ether, pH=8-10, Yield given. Multistep reaction Schoellkopf, Ulrich; Neubauer, Hans-Juergen; Synthesis; nb. 10; (1982); p. 861 - 864 View in Reaxys
O
N
O
H N O
O
NH 2 H
O
O
O
O
NH 2
O O
Rx-ID: 2585670 View in Reaxys 23/26 Yield
Conditions & References With hydrogenchloride, Ambient temperature Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
O
H
N
O N
O
H NH 2
O
O
H
NH 2 O
NH 2 O
O
Rx-ID: 3039190 View in Reaxys 24/26
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Yield
Conditions & References With hydrogenchloride, Ambient temperature Schoellkopf, Ulrich; Tetrahedron; vol. 39; nb. 12; (1983); p. 2085 - 2092 View in Reaxys
O
N
N
H 2N
OH
H
NH 2
H
O O
Rx-ID: 864613 View in Reaxys 25/26 Yield
Conditions & References in methanol, diethyl ether Pospisek,J.; Blaha,K.; Collection of Czechoslovak Chemical Communications; vol. 42; (1977); p. 1069 - 1076 View in Reaxys O H N
N
NH 2
HO
O
N HO
O
Rx-ID: 864872 View in Reaxys 26/26 Yield
Conditions & References (i) Et2O, (ii) Al-Hg, H2O, (iii) (racemate resolution using dibenzoyl-(R)-tartaric acid), Multistep reaction Pracejus,H.; Winter,S.; Chemische Berichte; vol. 97; (1964); p. 3173 - 3182 View in Reaxys
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