Iodoacetamide → 1,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH2:8]2.N1CCCC1.I[CH2:20][C:21]([NH2:23])=[O:22]>C1(C)C=CC=CC=1.O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH2:6][C:7]3[NH:23][C:21](=[O:22])[CH2:20][C:8]=3[C:9]=2[CH:10]=[CH:11][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
439 g (2.49 mol) of 5-methoxy-2-tetralone and 227 ml (3.67 mol) of pyrrolidine were dissolved in 3 l of toluene. After the addition of 16.4 g (0.09 mol) of p-toluenesulfonic acid monohydrate the mixture was boiled for 4 hours, whereby the resulting water was removed continuously using a water separator. Thereupon, the toluene was distilled off in a vacuum. The residue was dissolved in 1 l of tetrahydrofuran, whereupon a solution of 500 g (2.70 mol) of iodoacetamide in 2.5 l of tetrahydrofuran was added dropwise at room temperature. The mixture was boiled at reflux for 30 minutes, then cooled to room temperature and stirred for a further 12 hours. The solid was filtered off and washed with tetrahydrofuran. There were obtained 475 g (89%) of 1,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one as white crystals with m.p. 220°-222°.
Workup
- customwhereby the resulting water was removed continuously
- distillationThereupon, the toluene was distilled off in a vacuum
- additionwas added dropwise at room temperature
- temperatureat reflux for 30 minutes
- filtrationThe solid was filtered off
- washwashed with tetrahydrofuran
Sources & evidence
- ORD record
- ord-42f005d01a904aca95cd01e5feedb0de
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05318967
Reaction notes
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