Hydrochloric Acid → 2a-(4-Pentenyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one
Reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].Br[CH:17]=[CH:18][CH2:19][CH2:20][CH3:21].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:21]([C:3]12[CH2:12][CH2:11][CH2:10][C:5]3[C:4]1=[C:9]([CH:8]=[CH:7][CH:6]=3)[NH:1][C:2]2=[O:13])[CH2:20][CH2:19][CH:18]=[CH2:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
2a,3,4,5-Tetrahydro-1H-benz[cd]indol-2-one (4.0 g, 23 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 ml), and the solution was mixed with sodium hydride (760 mg, 190 mmol) and stirred at 0° C. for 1 hour. The reaction solution was mixed with 1-bromopentene (3.8 ml, 25 mmol) and stirred at −40° C. for 2 hours. Ethyl acetate, water and hydrochloric acid (1 N) were added to the reaction solution. The reaction product was extracted with ethyl acetate, washed with saturated brine and then dried with anhydrous sodium sulfate, and the material obtained by evaporating the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 2.7 g (11 mmol, 49% in yield) of the title compound.
Workup
- stirringstirred at −40° C. for 2 hours
- extractionThe reaction product was extracted with ethyl acetate
- washwashed with saturated brine
- dry with materialdried with anhydrous sodium sulfate
- customthe material obtained
- customby evaporating the solvent under a reduced pressure
- customwas separated
- custompurified by a silica gel column chromatography
- customto obtain
Sources & evidence
- ORD record
- ord-9af217dc1303420cbdc8750f4f8652a7
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498251B1
Reaction notes
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