Sodium Hydroxide → HCID 23296211, compound
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[Na+]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]Participants
Conditions
- Temperature
- -5 °C
Procedure
In a 5 liter three neck round bottom flask, 173 g (0.813 mol) of 7-bromo-1,2,3,4-tetrahydroisoquinoline was dissolved carefully into 950 mL of concentrated sulfuric add. The resulting solution was cooled to -5° C. and a solution of 82.7 g (0.816 mol) of potassium nitrate in 1 liter of concentrated sulfuric add was added dropwise. After addition, the reaction was maintained at -5° C. for 15 minutes and poured onto 3 liters of ice. The resulting mixture was basified to pH 14 with 50% sodium hydroxide solution. The basic solution was extracted three times with 1 liter of methylene chloride. The combined organic layers were washed with 1 liter each of water and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to yield 201 g of an oil. The oil, preadsorbed onto silica gel, was charged onto a column of 4 kg of silica gel and eluted with a gradient of 1-5% methanol/methylene chloride. The fractions containing product were combined and concentrated to yield 115 g of a solid.
Workup
- additionadd
- additionwas added dropwise
- additionAfter addition
- temperaturethe reaction was maintained at -5° C. for 15 minutes
- extractionThe basic solution was extracted three times with 1 liter of methylene chloride
- washThe combined organic layers were washed with 1 liter each of water and saturated sodium chloride solution
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6931e169caf4482eb93b7f99bae1345c
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121283
Reaction notes
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