Water → 5-Azido-5,6,7,8-tetrahydroquinoxaline
Reaction equation
Br[CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]1=2.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C=O)C>[N:12]([CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]1=2)=[N+:13]=[N-:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
5-bromo-5,6,7,8-tetrahydroquinoxaline, (Intermediate 20) (3.8 g, 17.92 mmol) and sodium azide (2.3 g, 35.8 mmol) were dissolved in DMF (50 mL) under nitrogen atmosphere and the reaction mixture was warmed to 60° C. for 20 hours. The mixture was cooled to room temperature and poured over water (200 mL), and was extracted with CH2Cl2 (3×100 mL). The organic extracts were washed with brine (2 ×100 mL), dried and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel using 1:1 EtOAc/hexanes to afford 5-azido-5,6,7,8-tetrahydroquinoxaline, (Intermediate 21) (3.2 g, 84%).
Workup
- temperatureThe mixture was cooled to room temperature
- extractionwas extracted with CH2Cl2 (3×100 mL)
- washThe organic extracts were washed with brine (2 ×100 mL)
- customdried
- concentrationconcentrated in vacuo
- customThe crude material was purified by flash column chromatography on silica gel using 1:1 EtOAc/hexanes
Sources & evidence
- ORD record
- ord-e53dd57ff4a044229094226b3c8aae18
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486969B2
Reaction notes
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