Triethylamine → (2-Methylindolizin-3-yl)(4-nitrophenyl)methanone

HRID 535469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535469
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]2[N:16]([CH:17]=1)[CH:15]=[CH:14][CH:13]=[CH:12]2.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:8][C:9]1[CH:10]=[C:11]2[N:16]([C:17]=1[C:25]([C:24]1[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:29][CH:28]=1)=[O:26])[CH:15]=[CH:14][CH:13]=[CH:12]2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 5826302-Methylindolizine

Produkt 1

HCID 23993764(2-Methylindolizin-3-yl)(4-nitrophenyl)methanoneAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

4.54 ml (32.52 mmol) of triethylamine are added, at ambient temperature under an inert atmosphere, to 3.56 g (27.14 mmoles) of 2-methylindolizine in 15 ml of dichloroethane, followed, dropwise, by 5.53 g (29.85 mmol) of 4-nitrobenzoic acid chloride. The reaction medium is stirred for 18 h at ambient temperature, hydrolysed with a saturated aqueous solution of sodium hydrogen carbonate and then extracted with dichloromethane. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, and then concentrated under reduced pressure. The residue obtained is washed with diethyl ether. 5.69 g of a yellow solid are obtained.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. washis washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e981ebb9cdac4c96b14e759f9ac107be
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859544B2

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