Nitric Acid → HCID 57437664、化合物

反応式

[CH3:1][C:2]1[N:3]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH:4]=[C:5]([CH3:7])[N:6]=1.[N+:16]([O-])([OH:18])=[O:17].C(=O)(O)[O-].[Na+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH3:1][C:2]1[N:3]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH3:7])[N:6]=1

参加物

反応条件

温度: 0 °C

実験手順

Compound 6 (6.82 grams, 34.5 mmol) was added in portions to trifluoroacetic anhydride (50 mL) cooled to 0° C. After 15 minutes the sodium chloride ice water bath was replaced with a dry ice acetone bath and nitric acid (6.0 mL 70%) was added drop wise. This was stirred to ambient temperature for 16 hours after which time it was pored into ice-water and neutralized with solid sodium bicarbonate. The product was extracted with dichloromethane and purified on a silica gel flash column eluted with 49:1 dichloromethane-methanol to give the desired product as an orange paste. LCMS data supported the structure.