Azobisisobutyronitrile → 5-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole
Reaction equation
Br[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=O)[CH2:27]C2>C(Cl)(Cl)(Cl)Cl>[CH3:21][O:22][C:23]1[CH:31]=[CH:30][C:29]2[CH:28]([CH3:27])[CH:5]3[CH2:6][NH:2][CH2:3][CH:4]3[C:25]=2[CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
N-bromosuccinimide (12.1 g, 67.9 mmol) and 2,2′-azobisisobutyronitrile (0.1 g, 0.6 mmol) were added to a solution of 5-methoxy-1-indanone (10.0 g, 61.7 mmol) in carbon tetrachloride (104 mL). The reaction mixture was stirred for 3 hours at 85° C. and then allowed to cool to room temperature. The reaction mixture was filtered through Celite, which was then washed with CH2Cl2 (100 mL). The filtrate was washed with brine (50 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C10H9BrO2+H: 241, observed: 241.
Workup
- temperatureto cool to room temperature
- filtrationThe reaction mixture was filtered through Celite, which
- washwas then washed with CH2Cl2 (100 mL)
- washThe filtrate was washed with brine (50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d62aedb0c2804d01addda72fcc039fb7
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716324B2
Reaction notes
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