Ammonium Hydroxide → HCID 178489909, Verbindung

HRID 862200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862200
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]=O)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C([O-])(=O)C.[NH4+:38].[OH-].[NH4+:40]>C(O)(=O)C>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[NH:38][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[N:40]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 187047601-(3-Methoxyphenyl)-2-pyridin-4-ylethane-1,2-dione

Produkt 1

HCID 178489909HCID 178489909, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1-(3-Methoxyphenyl)-2-pyridin-4-ylethane-1,2-dione (1.93 g, 8.0 mmol), 4-formylpiperidine-1-carboxylic acid tert-butyl ester (1.7 g, 8.0 mmol) and ammonium acetate (6.2 g, 80 mmol) were dissolved in acetic acid (20 mL) and heated to reflux for 2 hours, then allowed to cool to ambient temperature. The reaction mixture was poured over an ammonium hydroxide (50 mL) and ice mixture, extracted with ethyl acetate (3×125 mL) and the combined organic layers dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The resulting oil was chromatographed on silica gel eluting with ethyl acetate to give the imidazole as a foam (1.2 g), which was used without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×125 mL)
  4. dry with materialthe combined organic layers dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2f90c00743e84d3e98eb305821cda81f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05717100

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