Nitric Acid → HCID 15043299, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N+:13]([O-])([OH:15])=[O:14].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
5,8-dimethylquinoline (1.25 g), in a 250 mL round bottom flask is cooled to O° C. in an ice-NaCl bath under argon. Concentrated sulfuric acid (50 mL) is added slowly via addition funnel so that the internal temperature does not exceed 5° C. The solution is allowed to stir a few minutes then cooled to -15° C. in an ethylene glycol-dry ice bath. Nitric acid (1.7 mL, 69-71%) in sulfuric acid (50 mL) is added dropwise (via syringe) at such a rate that the reaction temperature does not exceed -3° C. After 10 minutes, the reaction is poured into a beaker of ice and basified slowly to pH 10 by the addition of ammonium hydroxide solution (28-30%). The product is extracted with ethyl acetate (3×500 mL). The organic layer is dried over MgSO4, filtered, and rotary evaporated to yield crude product (2.6 g) which is flash chromatographed on silica gel eluting with 15% ethyl acetate/hexane. Compound-containing fractions are combined and rotary evaporated to yield 5,8-dimethyl-6-nitroquinoline.
Workup
- customdoes not exceed 5° C
- customdoes not exceed -3° C
- extractionThe product is extracted with ethyl acetate (3×500 mL)
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- customrotary evaporated
- customto yield crude product (2.6 g) which
- customchromatographed on silica gel eluting with 15% ethyl acetate/hexane
- customrotary evaporated
Sources & evidence
- ORD record
- ord-ebe2cf0cdd254840896c281bf0b078e6
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05578607
Reaction notes
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