Nitric Acid → 3-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide
Reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[N+:13]([O-:15])=[O:14]Participants
Procedure
6.5 Grams of 3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide was added dropwise in a mixture consisting of 7 ml of fuming nitric acid and 7 ml of concentrated sulfuric acid under ice-cooled condition with stirring. The reaction mixture was stirred at 40° C. for 2 hours, then further stirred at 60° C. for 2 hours. The reaction mixture was poured in a cold aqueous solution of sodium hydroxide, then extracted with chloroform. The chloroform layer was washed with an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation, and the thus obtained residue was recrystallized from ethyl acetate-ethanol-n-hexane to yield 5.3 g of 3-methyl-4-nitro-5,6,7,8-tetrahydroquinoline-N-oxide.
Workup
- temperaturecooled condition
- stirringThe reaction mixture was stirred at 40° C. for 2 hours
- stirringfurther stirred at 60° C. for 2 hours
- extractionextracted with chloroform
- washThe chloroform layer was washed with an aqueous solution saturated with sodium chloride
- dry with materialdried with anhydrous magnesium sulfate
- customChloroform was removed by evaporation
- customthe thus obtained residue was recrystallized from ethyl acetate-ethanol-n-hexane
Sources & evidence
- ORD record
- ord-9aeb4166a4d2413e9d216d9e760cb6b7
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04738970
Reaction notes
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