Succinic anhydride → HCID 10250893, compound

Participants

Reaction Conditions

Reaction Steps

Pyridine (80 mL) was added to (7) (6.38 g, 20.7 mmol ) and succinic anhydride (3.11 g, 31.1 mmol ) and the reaction was heated under nitrogen at 80°-86° C. for 1.5 hours. Solvent was removed under high vacuum and the residue was dissolved with ether (150 mL) and washed with saturated NaHCO3 (4×50 mL). The aqueous portion was extracted with ether (2×50 mL), cooled to 0° C., acidified with cold 1N HCl (350 mL) and extracted with CHCl] (6×100 mL). A water wash (100 mL), solvent removal and flash column chromatography, eluting with 6% CH3OH/CH2Cl2, gave 7.46 g (88%) of (8) as a solid: mp 93°-94° C., NMR δ 1.2-1.8 (m+s, 16 H), 2.62 (s, 4 H), 2.9-3.2 (m, 2 H), 3.51-3.76 (m, 2 H), 4.8 (s, 2 H), 7.33 (s, 6 H). Anal. calcd. for C21H32N2O6 : C, 61.75; H, 7.90, N, 6.86. Found: C, 61.48; H, 7.90; N, 6.79.

Provenance & Evidence