Reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]=1.[OH-].[Na+].[N+:14]([O-])([OH:16])=[O:15]>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=2)[CH2:5][CH2:4][N:3]=1Participants
4
Procedure
1.0 g of 1-methyl-3,4-dihydroisoquinoline was dissolved in 7.0 ml of conc. nitric acid at 0° C., and 14.0 ml of fuming nitric acid was added dropwise to the solution. The solution was stirred for one hour at the same temperature, and overnight at room temperature. The reaction mixture was poured into ice, neutralized with aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The desiccant was separated by filtration, and the filtrate was purified by silica gel column chromatography to obtain 1.08 g of 1-methyl-7-nitro-3,4-dihydroisoquinoline, which was white crystal (yield: 82%).
Workup
- additionThe reaction mixture was poured into ice
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous solution of sodium chloride
- dry with materialdried with anhydrous sodium sulfate
- customThe desiccant was separated by filtration
- customthe filtrate was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-e24f2e9a41da499cbe6e9b9bc8c23963
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789595
Linked notes
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