反应详情

温度

110 °C

To a 50 mL flask were added 6 (0.25 g, 0.93 mmol), malonaldehyde dianilide hydrochloride (0.25 g, 0.97 mmol), acetic acid (4 mL) and acetic anhydride (4 mL). The mixture was heated at 110° C. for 90 min and then was cooled to rt. The volatile components were removed under vacuum to leave a tar. The tar was dissolved in acetic acid (4 mL) and then pyridine (5 mL) and 14 (0.34 g, 0.89 mmol) were added. The mixture was heated at 110° C. for 25 min and then cooled to rt. The volatile components were removed under vacuum to leave a dark blue tar that was dissolved in conc. HCl (20 mL). After stirring for 3 h, the mixture was diluted with water (150 mL) and then basified, first by addition of 4 M sodium hydroxide solution until the pH was approx. 4 and then with saturated sodium bicarbonate solution. The fluorescent product initially precipitated from the mixture but then re-dissolved. The aqueous solution was loaded onto a column of C-18 reverse-phase silica gel (4×15 cm) in water. The column was eluted with water to remove the salts and excess base, with 1 M HCl to generate the free acid of the fluorescent compound and then with water to remove the excess acid. Gradient elution from 0-55% methanol in water (5% steps of 500 mL-1 L) first eluted the symmetrical bisphosphonic acid fluorescent compound and then fluorescent compound 15. The fractions were evaporated in vacuo to leave a blue residue that was taken up in methanol (70 mL) and filtered through a medium frit. Water (30 mL) was added and then the solvent mixture was removed in vacuo to afford fluorescent compound 15 as a blue solid.

1. temperaturewas cooled to rt
2. customThe volatile components were removed under vacuum
3. customto leave a tar
4. temperatureThe mixture was heated at 110° C. for 25 min
5. temperaturecooled to rt
6. customThe volatile components were removed under vacuum
7. customto leave a dark blue tar that
8. customThe fluorescent product initially precipitated from the mixture
9. dissolutionre-dissolved
10. washThe column was eluted with water
11. customto remove the salts and excess base
12. customwith water to remove the excess acid
13. washGradient elution from 0-55% methanol in water (5% steps of 500 mL-1 L)
14. washfirst eluted the symmetrical bisphosphonic acid fluorescent compound
15. customThe fractions were evaporated in vacuo
16. customto leave a blue residue that
17. filtrationfiltered through a medium frit
18. additionWater (30 mL) was added
19. customthe solvent mixture was removed in vacuo