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2,6-Pyridinedicarboxylic acid → N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]acetamide

HRID 2268529
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268529
C[O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16]C)=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:7]2.N1C(C(O)=O)=CC=CC=1C(O)=O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O.C(OCC)(=O)C>[CH3:13][O:12][C:11]1[C:3](=[O:2])[C:4]2[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH2:7][C:8]=2[C:9](=[O:16])[C:10]=1[O:14][CH3:15]
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Komponenten

7

Edukt 3

HCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 18348615N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]acetamide

Produkt 1

HCID 18348613N-[8-(5,6-Dimethoxy-4,7-dioxoindan-2-yl)octyl]acetamideAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
2×
HCID 6342AcetonitrileLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of N-[8-(4,5,6,7-tetramethoxyindan-2-yl)octyl]acetamide (700 mg), 2,6-pyridinedicarboxylic acid (857 mg), acetonitrile (7.0 ml), ethyl acetate (7.0 ml), and water (7.0 ml) was dropwise added a solution of CAN (3.75 g) in acetonitrile (3.5 ml) and water (3.5 ml) with cooling with ice. After being stirred for 15 min, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate) and then with recrystallization from hexane-ethyl acetate) to yield the entitled compound (495 mg) as crystals.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customwith recrystallization from hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1fbbb0fbb3e34e8c80f12d3205c5e1f5
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

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