Acetic Acid → HCID 15719366, compound

Participants

Reaction Steps

A solution of 1a (5.84 g, 10.5 mmol) in 400 mL of ethanolic ammonia (saturated at 0° C.) was sealed in a glass-lined stainless steel bomb and left at room temperature for 3 days. The solution was evaporated to dryness and evaporated with ethanol to remove ammonia. The residue, containing the desired product and 5'-benzoyl compound, was dissolved in 440 mL of acetonitrile and 120 mL of water. Lithium hydroxide monohydrate (881 mg, 21 mmol) was added, and the solution was stirred for 16 hours at room temperature. Thin-layer chromatography (5:1 CHCl3 -MeOH) indicated complete reaction. The chilled solution was carefully neutralized with glacial acetic acid and evaporated to dryness. The white solid residue was recrystallized from water. The product was dried in vacuo at room temperature at 100° C. for 2 hours: 2.15 g (59.2%). Mp 209-210° C., TLC 5:1 CHCl3 -MeOH Rf 0.47; HPLC 99.8% 9:1; H2O-MeCN; MS, 3.48 (M+1)+ ; UV λmax pH 1 264 (14.3), pH 7 264 (14.9), pH 13 264 (15.2). Anal. Calcd. for C10H11BrFN5O3 : C, 34.50; H, 3.18; N, 20.12. Found: C, 34.36; H, 3.28; N, 19.93.

Provenance & Evidence