Reaktion #10074

Reaktionsgleichung

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

2-methoxyacetyl chloride

→

product

Ausbeute 100.0%

N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]-2-methoxyacetamide

Ausbeute 100.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a 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 2-methoxyacetyl chloride (0.43 g, 4.0 mmol). The stirred 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 0.69 g (100%) of product as an off-white solid: mp 246–248° C.; 1H NMR (DMSO-d6) δ 11.15 (s, 1H), 10.30 (s, 1H), 8.70 (d, J=8.4 Hz, 1H), 7.86 (t, J=7.8 Hz, 1H), 7.63 (d, J=7.3 Hz, 1H), 5.17 (dd, J=5.2 and 12.7 Hz, 1H), 4.11 (s, 2H), 3.49 (s, 3H), 2.98–2.84 (m, 1H), 2.66–2.47 (m, 2H), 2.12–2.07 (m, 1H); 13C NMR (DMSO-d6) δ 172.67, 169.66, 169.02, 168.25, 166.61, 136.48, 135.91, 131.24, 124.35, 118.31, 116.04, 71.40, 59.10, 48.96, 30.91, 21.94; Anal. Calcd. For C16H15N3O6: C, 55.65; H, 4.38; N, 12.17. Found: C, 55.58; H, 4.40; N, 12.08.

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