Water → 2,3-dihydro-6-methoxy-2-(3-pyridylmethyl)-1H-isoindole-1-one

HRID 1609597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609597
[H-].[Na+].C(O[CH2:7][C:8]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:11])(=O)C.O.C1(C)C=CC=CC=1>CN(C)C=O>[CH3:25][O:24][C:21]1[CH:20]=[C:9]2[C:8]([CH2:7][N:12]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:10]2=[O:11])=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 24758Sodium hydrideHCID 200820032-acetoxymethyl-5-methoxy-N-(3-pyridylmethyl)benzamide

Produkt 1

HCID 200820092,3-dihydro-6-methoxy-2-(3-pyridylmethyl)-1H-isoindole-1-oneAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 136 mg of sodium hydride (about 60%) in 7 ml of dimethylformamide chilled at 0° C. was added 820 mg of 2-acetoxymethyl-5-methoxy-N-(3-pyridylmethyl) benzamide and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was mixed with water and shaken with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate to give 386 mg of the titled compound.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was chromatographed on a column of silica gel
  5. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ba36a531530d4f389bd800a5fdd62bce
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05401756

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