تفاعل #43997

معادلة التفاعل

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

المردود 15.0%

المذيبات

DMF

Acetic acid

carbon tetrachloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux under nitrogen for 45 min
3. 3
   أخرىilluminating with a 200 W lamp
4. 4
   درجة الحرارةthe mixture refluxed for 3 h under nitrogen
5. 5
   أخرىthe reaction evaporated to dryness under vacuum
6. 6
   أخرىThe product was partially purified by SPE (NH2, 10 g)
7. 7
   غسيلeluting with methanol
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   غسيلwashing with 5% acetic acid in methanol
10. 10
    أخرىAfter evaporation of the solvents under vacuum
11. 11
    غسيلeluting with a gradient (1:1 ethyl acetate/cyclohexane to 5% methanol, 1% acetic acid in 1:1 ethyl acetate/cyclohexane)

الإجراء التجريبي

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%).

المصدر