Aluminum(III) Chloride → 3-methyl-1-phenylindolin-2-one
Reaction equation
Cl[CH:2]([CH3:18])[C:3]([N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:18][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]1=[O:4]Participants
Conditions
- Temperature
- 190 °C
Procedure
A mixture of 13.3 g (0.00513 mole) of N-(2-chloropropanoyl)-diphenylamine and 14.7 g (0.011 mole) of anhydrous aluminum chloride was stirred for 10 minutes while heating over an oil bath of 190° C. The reaction mixture was poured into 10% hydrochloric acid-ice, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with 10% hydrochloric acid, water, a sodium hydrogen carbonate aqueous solution and then water, and dried over anhydrous sodium sulfate. Ethyl acetate was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:5 (v.v))) and then recrystallized from hexane to obtain 9.54 g of the title compound as pale yellow crystals. Melting point: 77° to 78° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed successively with 10% hydrochloric acid, water
- dry with materiala sodium hydrogen carbonate aqueous solution and then water, and dried over anhydrous sodium sulfate
- customEthyl acetate was removed under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:5 (v.v)))
- customrecrystallized from hexane
Sources & evidence
- ORD record
- ord-6e426a9c16f2465087b3f501bff8a483
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434148
Reaction notes
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