p-Aminophenylacetic acid ethyl ester → ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 15720

Reaktionsgleichung

Reaktionsgleichung von HRID 15720
Br[CH2:2][C:3]1[C:12]([CH2:13]Br)=[C:11]([O:15][CH2:16][CH3:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[O:18][CH2:19][CH3:20].[CH2:21]([O:23][C:24](=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH3:22]>CN(C)C=O>[CH2:21]([O:23][C:24](=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:13][C:12]3[C:11]([O:15][CH2:16][CH3:17])=[C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[C:4]([O:18][CH2:19][CH3:20])[C:3]=3[CH2:2]2)=[CH:30][CH:31]=1)[CH3:22]

Komponenten

4

Edukt 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 210793342,3-Bis(bromomethyl)-1,4-diethoxy-naphthalene

Produkt 1

HCID 131726211ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2,3-bis(bromomethyl)-1,4-diethoxy-naphthalene (41 mg, 0.1 mmol) and 4-aminophenylacetic acid ethyl ester (20 mg, 0.11 mmol) in N,N-dimethylformamide (1 ml) was heated at 60° C. under nitrogen for 14 h. The solvent was removed in vacuo and the residue taken up in ethyl acetate (10 ml) and washed with 8% aqueous sodium bicarbonate solution (5 ml). The organic layer was dried over magnesium sulphate and the solvent removed in vacuo. Purification by flash column chromatography on silica gel eluting with 90% cyclohexane/ethyl acetate gave the product as a white solid (15 mg, 36%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washwashed with 8% aqueous sodium bicarbonate solution (5 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customthe solvent removed in vacuo
  5. customPurification by flash column chromatography on silica gel eluting with 90% cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-053c8e8e62434c409462a28dcbd344c3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732622B2

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