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Hydrochloric Acid → HCID 59146144, Verbindung

HRID 1512790
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512790
O.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][N+:30]([O-])=O)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>CCOC(C)=O.CO.[Fe]>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][NH2:30])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]
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Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 591460297-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3-(2-nitroethyl)-1H-indole

Produkt 1

HCID 59146144HCID 59146144, VerbindungAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysator
HCID 887
Methanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Water (20 mL) and concentrated HCl solution (10 mL) were added to a solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3-(2-nitroethyl)-1H-indole (D83) (2.1 g) in EtOAc (70 mL) and methanol (150 mL). The mixture was heated to reflux and stirred efficiently. Fe (6.0 g) was added in portions. After the addition was complete, the reaction mixture was refluxed for 8 hours. The solid was filtered off and the filtrate was concentrated and then basified with saturated NaHCO3 solution. The solid was filtered off and the filtrate was extracted with dichloromethane (200 mL). The organic layer was washed with water and brine, and then dried over MgSO4. Removal of the solvent gave the product 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]ethanamine (D84) (1.4 g) as a yellow foam solid. No further purification was carried out. MS (ES): C21H21ClN4O2 requires 396; found 397.2 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. additionAfter the addition
  4. temperaturethe reaction mixture was refluxed for 8 hours
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate was concentrated
  7. filtrationThe solid was filtered off
  8. extractionthe filtrate was extracted with dichloromethane (200 mL)
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried over MgSO4
  11. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-e4ce68fe07e947b89a641d7887b9282b
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217028B2

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