p-Aminophenylacetic acid ethyl ester → ethyl[4-(4,9-diethoxy-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate
Reaktionsgleichung
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
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
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%).