Hydrochloric Acid → 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one
Reaction equation
[Br-].[Al+3].[Br-].[Br-].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:10]([CH:12]2[C:16](=O)[CH2:15][N:14]([CH3:18])[C:13]2=[O:19])[CH:11]=1.O.Cl>ClC1C=CC=CC=1Cl.CCCCCC>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:16]3[CH2:15][N:14]([CH3:18])[C:13](=[O:19])[C:12]=3[C:10]=2[CH:11]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
Anhydrous aluminium bromide (2.5 g) was added to a reaction mixture containing 3-(5-chloro-2-phenoxyphenyl)-1-methylpyrrolidine-2,4-dione (1 g) in 1,2-dichlorobenzene (4 mL) at ambient temperature. The reaction mixture was stirred at about 85° C. for about 9 hours, then cooled to ambient temperature. A mixture of water and concentrated hydrochloric acid (50 mL:5 mL) was added slowly. The contents were stirred for about 30 minutes. Hexane (10 mL) was added. The contents were stirred for about 1 hour, filtered, washed with hexane (10 mL) and dried in air at about 30° C. for about 15 hours to obtain 11-chloro-2-methyl-2,3-dihydro-1H-dibenzo [2,3:6,7]oxepino[4,5-c]pyrrol-1-one.
Workup
- temperaturecooled to ambient temperature
- additionwas added slowly
- stirringThe contents were stirred for about 30 minutes
- stirringThe contents were stirred for about 1 hour
- filtrationfiltered
- washwashed with hexane (10 mL)
- customdried in air at about 30° C. for about 15 hours
Sources & evidence
- ORD record
- ord-67eb6d69493a4e2d895a6d6260032cc9
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145421B2
Reaction notes
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