반응 #43997

반응 방정식

Sodium metabisulphite

4-aminophenyl acetic acid

triethylamine

ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate

N-bromosuccinimide

dibenzylperoxide

→

[4-(4,9-dimethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid

수율 15.0%

용매

DMF

Acetic acid

carbon tetrachloride

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux under nitrogen for 45 min
3. 3
   기타illuminating with a 200 W lamp
4. 4
   온도the mixture refluxed for 3 h under nitrogen
5. 5
   기타the reaction evaporated to dryness under vacuum
6. 6
   기타The product was partially purified by SPE (NH2, 10 g)
7. 7
   세척eluting with methanol
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   세척washing with 5% acetic acid in methanol
10. 10
    기타After evaporation of the solvents under vacuum
11. 11
    세척eluting with a gradient (1:1 ethyl acetate/cyclohexane to 5% methanol, 1% acetic acid in 1:1 ethyl acetate/cyclohexane)

실험 절차

To a solution of ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate (73 mg, 0.266 mmol) in carbon tetrachloride (10 ml) was added N-bromosuccinimide (47 mg, 0.266 mmol) and dibenzylperoxide (5 mg). The mixture was heated at reflux under nitrogen for 45 min, illuminating with a 200 W lamp. The reaction was cooled to room temperature, 4-aminophenyl acetic acid (40 mg, 0.266 mmol), triethylamine (74 μl, 0.53 mmol) and DMF (5 ml) added and the reaction stirred for 48 h. Acetic acid (glacial, 1 ml) was added to the reaction and the mixture refluxed for 3 h under nitrogen. Sodium metabisulphite solution (1 ml) was added and the reaction evaporated to dryness under vacuum. The product was partially purified by SPE (NH2, 10 g) eluting with methanol then 5% acetic acid in methanol. The fractions containing product were passed through a silica plug washing with 5% acetic acid in methanol. After evaporation of the solvents under vacuum, the residue was columned on a silica gel flash column eluting with a gradient (1:1 ethyl acetate/cyclohexane to 5% methanol, 1% acetic acid in 1:1 ethyl acetate/cyclohexane) to give [4-(4,9-dimethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid (15 mg, 15%).

출처