Sodium Hydroxide → ethyl [4-(4-methoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 15722

Reaktionsgleichung

Reaktionsgleichung von HRID 15722
O[CH:2]1O[C:5](=[O:7])[C:4]2[CH:8]=[C:9]3[C:14](=[C:15]([O:16][CH3:17])[C:3]1=2)[CH:13]=[CH:12][CH:11]=[CH:10]3.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][C:22]1[CH:21]=[CH:20][C:19]([N:18]2[C:5](=[O:7])[C:4]3[CH:8]=[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]4=[C:15]([O:16][CH3:17])[C:3]=3[CH2:2]2)=[CH:24][CH:23]=1)[CH3:30]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 210793353-hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one

Produkt 1

HCID 86612034ethyl [4-(4-methoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetateAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one (50 mg, 0.22 mmol) and ethyl 4-aminophenylacetate (47 mg, 0.26 mmol) in dichloromethane (5 ml) were stirred at room temperature under nitrogen for 1 hour. Sodium triacetoxyborohydride (138 mg, 0.66 mmol) was added and stirring continued for 24 h. The reaction was adjusted to pH14 with sodium hydroxide solution (2N) and extracted with dichloromethane (3×5 ml). The combined extracts were evaporated under vacuum and the residue triturated with cyclohexane/ether to give ethyl[4-(4-methoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate as a white solid (45 mg, 54%).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×5 ml)
  2. customThe combined extracts were evaporated under vacuum
  3. customthe residue triturated with cyclohexane/ether

Quellen und Nachweise

ORD-Eintrag
ord-780617ed16d1496c8b8e69f04c32cc69
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732622B2

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