Nitric Acid → Spiro(5-nitroindane)-2,5'-hydantoin
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]21[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10]2.[N+:16]([O-])([OH:18])=[O:17]>>[N+:16]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][C:2]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10]1)[CH2:3]2)([O-:18])=[O:17]Participants
3
Procedure
A solution of (±)-spiro[imidazolidine-4,2′-indane]-2,5-dione (3.0 g, 14.8 mmol, described in Intermediate 12) in conc. nitric acid (33 mL) was stirred at ambient temperature for 1 h. The reaction was then poured onto crushed ice and the resultant solid was isolated by filtration. The crude material was recrystallized from ethanol to give the title compound as a yellow solid. MS: m/z=248 (M+1).
Workup
- additionThe reaction was then poured
- customonto crushed ice
- customthe resultant solid was isolated by filtration
- customThe crude material was recrystallized from ethanol