Reacción #2175460

Ecuación de reacción

2,7-di(3-carboxy-propionyl)fluorene

HCl

NaOH

hydrazine hydrate

→

2,7-di(3-carboxy-propyl)fluorene

Disolventes

diethylene glycol

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas placed in a room temperature
2. 2
   Temperaturarefluxed for approximately two hours
3. 3
   OtroAfter three hours at 200° C. reaction temperature the reaction
4. 4
   Temperaturawas cooled to approximately 60° C
5. 5
   FiltraciónThe product was filtered
6. 6
   Lavadowashed with water
7. 7
   workup.DISSOLUTIONThe product was dissolved in warm NaOH solution (0.5M)
8. 8
   Otroprecipitated by acidification to pH 2 with HCl
9. 9
   FiltraciónThe product was filtered
10. 10
    Lavadowashed with water (Yield 10.9 g, 92%)

Procedimiento

In an argon-purged flask 2,7-di(3-carboxy-propionyl)fluorene (12.8 g, 0.035 mol) was suspended in diethylene glycol (150 mL). The flask was placed in a room temperature oil bath then NaOH (14 g, 0.35 mol) and an 80% solution of hydrazine hydrate (13.1 mL, 0.21 mol) were added successively. The reaction mixture was slowly heated to 110° C. and refluxed for approximately two hours. The reaction temperature was raised to 200° C. with removal of water during the heating process. After three hours at 200° C. reaction temperature the reaction was cooled to approximately 60° C. The reaction mixture was carefully poured into water (500 mL) and the mixture was acidified to pH 2 with concentrated HCl. The product was filtered and washed with water. The product was dissolved in warm NaOH solution (0.5M) and precipitated by acidification to pH 2 with HCl. The product was filtered and washed with water (Yield 10.9 g, 92%). 1H-NMR (d6-DMSO): δ (ppm) 12.0 (s, 2H, COOH); 7.8 (m, 2H, Ar); 7.4 (s, 2H, Ar); 7.2 (m, 2H, Ar); 3.9 (s, 2H, CH2); 2.7 (t, 4H, CH2); 2.3 (t, 4H, CH2); 1.8 (m, 4H, CH2).

Fuente