Ammonia → HCID 131723472, compound

Participants

Reaction Conditions

Reaction Steps

First, 4-(dimethyl amino) pyridine (31.1 mg) was added to 9.1 ml pyridine, before adding succinic anhydride (487.7 mg). Borneol (168.4 mg) was added last, and the reaction mixture was heated under reflux with stirring for 53 hr at 65° C. The reaction was monitored by thin layer chromatography (“TLC”). The TLC assay used silica gel 60 F264 aluminum sheets (0.2 mm thick) from E. Merck (Darmstadt, Germany) with a mobile phase of 100 % ethyl acetate, 100% methanol, and 1% aqueous ammonia in a ratio of 80:20:1. The resulting bands were visualized by adding a mixture of 100% anisaldehyde, 100% acetic acid, and 100% sulfuric acid in a ratio of 0.5:50:1. The reaction was stopped with 20 ml H2O. The resultant product was extracted three times, each time with 25 ml methylene chloride. The organic layer was collected from each extract, pooled, rotaevaporated to dryness, and then dried under vacuum in the presence of phosphorous pentoxide. The product produced was boreol-hemisuccinate.

Provenance & Evidence