Sodium Hydroxide → 8-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulene-5-carboxylic acid amide

HRID 25342

Reaktionsgleichung

Reaktionsgleichung von HRID 25342
[CH3:1][N:2]([CH3:18])[CH:3]1[C:12]2[CH2:11][O:10][C:9]([C:13]#[N:14])=[CH:8][C:7]3=[CH:15][NH:16][CH:17]=[C:5]([C:6]=23)[CH2:4]1.[OH-:19].[Na+]>>[CH3:1][N:2]([CH3:18])[CH:3]1[C:12]2[CH2:11][O:10][C:9]([C:13]([NH2:14])=[O:19])=[CH:8][C:7]3=[CH:15][NH:16][CH:17]=[C:5]([C:6]=23)[CH2:4]1

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 697371988-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbonitrile

Produkt 1

HCID 697364658-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulene-5-carboxylic acid amideAusbeute 62 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Polyphophoric acid 420 mg was added to compound (48) 31.6 mg under an argon atmosphere and the mixture was heated at 90° C. for 6 h. Ice-water was added to the reaction mixture, which was made alkaline with an aqueous 5 N-sodium hydroxide solution and extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:methanol (97:3) to give the titled compound as colorless crystals, 20.9 mg. Yield 62%. Furthermore, the titled compound was recrystallized from acetone-isopropyl ether to give colorless crystals, m.p. 182-183° C.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas chromatographed on aluminum oxide in chloroform:methanol (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-f83712f482374db8bbb5f7143921623f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858640B2

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