Acrylamide → 1,3,4,9-Tetrahydro-indeno[2,1-b]pyridin-2-one
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[N:10]1[CH2:14][CH2:13][CH2:12]C1.C(N)(=[O:18])C=C>C(O)(=O)C.O>[NH:10]1[C:14](=[O:18])[CH2:13][CH2:12][C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:1][C:2]1=2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-(1H-inden-2-yl)-pyrrolidine (5.34 g) and acrylamide (6.15 g) is stirred in argon atmosphere at 100° C. for 30 min. The temperature is then raised to 130° C. and stirring continued for another 15 min. After cooling to room temperature, water (50 mL) and acetic acid (5 drops) are added and the mixture is stirred for 30 min. The mixture is filtered and the organic phase of the filtrate is separated and washed with brine. After drying (MgSO4) and evaporating the solvent, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to give a brown solid that is triturated with ethyl acetate and dried to afford the title compound. Yield: 1.12 g (21% of theory); Mass spectrum (ESI+): m/z=186 [M+H]+.
Workup
- temperatureThe temperature is then raised to 130° C.
- stirringstirring
- waitcontinued for another 15 min
- temperatureAfter cooling to room temperature
- stirringthe mixture is stirred for 30 min
- filtrationThe mixture is filtered
- customthe organic phase of the filtrate is separated
- washwashed with brine
- dry with materialAfter drying (MgSO4)
- customevaporating the solvent
- customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)
- customto give a brown solid that
- customis triturated with ethyl acetate
- customdried
Sources & evidence
- ORD record
- ord-53ef48b2a70a407fb4fc532ed7fcd070
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686149B2
Reaction notes
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