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3-Methoxyaniline → HCID 68897788, Verbindung

HRID 900319
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 900319
[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16](SC)=[N:17][CH:18]=[N:19]3)[CH2:9][C@@H:8]1[C:26]([O:28][CH3:29])=[O:27])=[O:6])[CH:2]=[CH2:3].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35]>CC#N.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[C:32]([O:31][CH3:30])[CH:33]=2)=[N:17][CH:18]=[N:19]3)[CH2:9][C@@H:8]1[C:26]([O:28][CH3:29])=[O:27])=[O:6])[CH:2]=[CH2:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 108243-MethoxyanilineHCID 68900372HCID 68900372, Verbindung

Produkt 1

HCID 68897788HCID 68897788, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 15B (453 mg, 1.05 mmol), 3-methoxyaniline (142.5 mg, 1.16 mmol) in CH3CN (25 ml) was added AgNO3 (197 mg, 1.16 mmol). The mixture was heated at 70° C. for 30 min. After cooling to room temperature, the solid was removed by filtration through a pad of Celite and the filtrate was concentrated in vacuo. The residue was taken into with water, treated with saturated NaHCO3 and extracted with EtOAc (×3). The combined extracts were dried over anhydrous Na2SO4. Concentration in vacuo gave 644 mg of crude 15C as an oil, which was used in next step without further purification. The compound has an analytical HPLC retention time=2.259 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=506+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe solid was removed by filtration through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additiontreated with saturated NaHCO3
  5. extractionextracted with EtOAc (×3)
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a2152741b20f4f6a9f5674a207a9bd33
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07358256B2

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