Sulfuric Acid → 5-Bromo-8-nitroquinoline
Reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2.OS(O)(=O)=O>>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2Participants
4
Procedure
KNO3 (1.58 g, 15.6 mmol) was added portionwise to a solution of 5-bromoquinoline (2.0 g, 12.0 mmol) conc.H2SO4 (7.5 ml) at 0° C. and the mixture was stirred at room temperature for 16 h. The mixture was poured onto ice and the resulting solid was extracted into DCM. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (2.8 g, 92%) which was used in the next step without further purification.
Workup
- additionThe mixture was poured onto ice
- extractionthe resulting solid was extracted into DCM
- washThe organic phase was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-aa03e42816884cf8abb18e9940d8fa0b
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102688B2
Reaction notes
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