Hydrochloric Acid → HCID 22310837, Verbindung

HRID 967099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967099
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:19]([O:21]C)=[O:20].[I-].[Li+].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:19]([OH:21])=[O:20]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 22310834HCID 22310834, Verbindung

Produkt 1

HCID 22310837HCID 22310837, VerbindungAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Methyl N-(3,4-Dichlorobenzyl)-5-acetylaminoindole-2-carboxylate (88 mg) and lithium iodide (300 mg) were dissolved in pyridine and heated at reflux for 8 hours, then cooled to room temperature and poured into 2M HCl and extracted with diethyl ether. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography using DCM-2% methanol as eluent to give the desired end product as a white solid (19 mg, 22%), mp 245-246°; NMR δ (CD3SOCD3) 2.02 (s, 3H), 5.82 (s, 2H), 6.90 (d, 1H), 7.20-7.55 (m, 5H), 8.02 (s, 1H), 9.83 (s, 1H); M/z (+) 377 (MH+), 278.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. extractionextracted with diethyl ether
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ba03778e3c7424e94cc40a914e612b6
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953809B2

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