Sodium Azide → ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate
Reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[N-:15]=[N+]=[N-].[Na+]>CS(C)=O>[NH:15]1[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[CH:8]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
To a mixture of ethyl 3-(2-chlorocyclohex-1-enyl)acrylate (21.4 g, 100 mmol) in DMSO (100 mL) was added sodium azide (9.75 g, 150 mmol). The reaction mixture was heated at 105° C. for 4 h. After cooling to room temperature, the mixture was poured into ice water. The resulting precipitate was collected by filtration to afford 121a (18.0 g, 93.3%). MS-ESI: [M+H]+ 194.
Workup
- temperatureAfter cooling to room temperature
- filtrationThe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-79a63a4d650948a99e4cc0ed9d2800b5
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115152B2
Reaction notes
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