Hydrochloric Acid → 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

HRID 2284359Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[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]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Anhydrous aluminium chloride (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 (5 mL) at ambient temperature. The reaction mixture was stirred at about 85° C. for about 2 hours and 30 minutes, then cooled to ambient temperature. A mixture of water and concentrated hydrochloric acid (50 mL:5 mL) was added dropwise. The contents were stirred for about 30 minutes. Hexane (10 mL) was added. The contents were stirred for about 15 minutes, filtered, washed with hexane (10 mL) and dried in air at about 30° C. for about 15 hours followed by further drying at about 50° C. under reduced pressure 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 dropwise
stirringThe contents were stirred for about 30 minutes
stirringThe contents were stirred for about 15 minutes
filtrationfiltered
washwashed with hexane (10 mL)
customdried in air at about 30° C. for about 15 hours
customby further drying at about 50° C. under reduced pressure

Sources & evidence

ORD record: ord-a7d651ffb97a4dcf8e64135d1d2bfb91
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145421B2

Reaction notes

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