Reaktion #10076

Reaktionsgleichung

4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione

(chlorocarbonyl)methyl acetate

→

product

Ausbeute 75.0%

{N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]carbamoyl}methyl acetate

Ausbeute 75.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux for 18 hours
3. 3
   SonstigeThe solvent was evaporated in vacuo
4. 4
   Filtrationfiltered

Vorschrift

To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added (chlorocarbonyl)methyl acetate (0.55 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filtered to give 0.56 g (75%) of product as an off-white solid: mp 234–236° C.; 1H NMR (DMSO-d6) δ 11.15 (s, 1H), 10.06 (s, 1H), 8.55 (d, J=8.3 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 5.17 (dd, J=5.0 and 12.4 Hz, 1H), 4.78 (s, 2H), 2.99–2.85 (m, 1H), 2.65–2.52 (m, 2H), 2.22 (s, 2H), 2.11–2.07 (m, 1H); 13C NMR (DMSO-d6) δ 172.70, 169.69, 169.50, 167.99, 166.57, 136.40, 135.59, 131.35, 125.34, 118.72, 116.96, 62.60, 48.98, 30.90, 21.91, 20.41; Anal. Calcd. For C17H15N3O7: C, 54.69; H, 4.05; N, 11.26. Found: C, 54.43; H, 4.05; N, 10.97.

Quelle