反应详情

To a stirred solution of 4-hydrazinobenzenesulfonic acid (Aldrich, 11.25 g, 0.06 mol) in acetic acid (50 ml) was added 7-acetyloctanoic acid (16.7 g, 0.09 mol). The reaction mixture was heated under reflux for 12 hrs. Acetic acid was removed under reduced pressure. The resulting solid was dissolved in methanol and reprecipitated with a saturated solution of potassium hydroxide in isopropanol. The solid was filtered, washed with isopropanol and dried, (8 g, 40%). The analytical sample was obtained by C18 reversed phase column chromatography using water/methanol mixture as solvent, m.p. 250° C. dec; IR ν cm−1=2930, 2597, and 1719. 1H NMR, D2O, δ, 7.8-7.9 (m, 2H, 4-H and 6-H of aromatic protons); 7.6 (d, J=7 Hz, 1H, 7-H of aromatic); 2.2 (t, J=7 Hz, 2H, —CH2—COOH); 1.9-2.1 (m, 2H, alkyl); 1.2-1.6 (a singlet merged in a multiplet, 7H, —CH3, (—CH2)2); 0.6-0.9 (m, 2H, alkyl.).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 12 hrs
3. customAcetic acid was removed under reduced pressure
4. dissolutionThe resulting solid was dissolved in methanol
5. customreprecipitated with a saturated solution of potassium hydroxide in isopropanol
6. filtrationThe solid was filtered
7. washwashed with isopropanol
8. customdried
9. customThe analytical sample was obtained by C18 reversed phase column chromatography