Nitric Acid → 6-bromo-7-methyl-8-nitroquinazolin-4(3H)-one
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[CH:7][NH:6][C:5]2=[O:13].OS(O)(=O)=O.[N+:19]([O-])([OH:21])=[O:20]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:19]([O-:21])=[O:20])[C:11]=1[CH3:12])[N:8]=[CH:7][NH:6][C:5]2=[O:13]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
6-Bromo-7-methylquinazolin-4(3H)-one (1.0 g, 4.2 mmol) was added to H2SO4 (98%, 15 mL) and the mixture was stirred at it until dissolution was complete. The mixture was cooled to 0° C. and then nitric acid (fuming) (0.26 g, 4.2 mmol) was added dropwise at 0° C. and stirred for 10 min, and then stirred at it for 5 h. The mixture was poured onto ice (300 g) and extracted with EtOAc (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo. The product was recrystallized from MeOH (˜15 mL). MS (ESI, pos. ion) m/z: 284 [M+H]+
Workup
- stirringstirred for 10 min
- stirringstirred at it for 5 h
- additionThe mixture was poured onto ice (300 g)
- extractionextracted with EtOAc (3×80 mL)
- washThe combined organic layers were washed with brine (100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe product was recrystallized from MeOH (˜15 mL)
Sources & evidence
- ORD record
- ord-9bc92ab3949043838aa632df4c35634b
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557830B2
Reaction notes
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