Ammonia → HCID 69587602, compound

Participants

Reaction Steps

To a solution of the product from Step C (1.61 g, 7.76 mmol) in methanol (20 mL) was added dimethyl oxalate (9.16 g, 77.6 mmol), p-toluene sulfonic anhydride hydrate (50 mg), and the mixture was heated to distill off liquids with a bath temperature of 120° C. for 5 h. The dark residue was treated with methanolic ammonia (7 M, 22 mL, 0.15 mol) and heated at reflux temperature for 1 h. Additional ammonia (7 M in methanol, 20 mL) was added and heating continued for another hour. The reaction mixture was cooled to room temperature, filtered, and evaporated to a brown solid that was purified by chromatography to give a tan solid (0.91 g, 45%): LC/MS m/z 279.

Provenance & Evidence