Butyryl chloride → 5-Butyryl-2-indolinone
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18]>ClCCCl>[C:15]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][C:6](=[O:14])[CH2:7]2)(=[O:19])[CH2:16][CH2:17][CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 15 g aluminum chloride suspended in 30 mL 1,2-dichloro-ethane in an ice bath was added 7.5 g of 2-oxindole and then 12 g of butanoyl chloride. The resulting suspension was heated to 50° C. overnight. The mixture was poured into ice water and extracted 3 times with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate, and concentrated to dryness to give a brown solid. The solid was chromatographed on silica gel (50% ethyl acetate in hexane) to give 3 g (25%) of the title compound as a yellow solid. 5-Cyanoethyl-2-oxindole Potassium cyanide (2.0 g) was added to 15 mL of dimethyl-sulfoxide and heated to 90° C. 5-Chloroethyl-2-oxindole (3.0 g) dissolved in 5 mL dimethyl sulfoxide was added slowly with stirring, and the reaction heated to 150° C. for 2 hours. The mixture was cooled, poured into ice water and the precipitate collected by vacuum filtration, washed with water, dried and then chromatographed on silica gel (5% methanol in chloroform) to give 1.2 g (42% yield) of the title compound.
Workup
- extractionextracted 3 times with ethyl acetate
- washThe combined ethyl acetate layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness
- customto give a brown solid
- customThe solid was chromatographed on silica gel (50% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-85887f8781b14e25964f4cfbca005504
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579897B2
Reaction notes
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