Dimethyl Sulfoxide → 5-Butyryl-2-indolinone
Reaction equation
[C-]#N.[K+].[C:4]([CH2:6]CC1C=C2C(=CC=1)NC(=O)C2)#N.Cl[CH2:19][CH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2.CS(C)=[O:33]>>[C:20]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2)(=[O:33])[CH2:19][CH2:4][CH3:6]Participants
Conditions
- Temperature
- 90 °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
- additionwas added slowly
- temperaturethe reaction heated to 150° C. for 2 hours
- temperatureThe mixture was cooled
- filtrationthe precipitate collected by vacuum filtration
- washwashed with water
- customdried
- customchromatographed on silica gel (5% methanol in chloroform)
Sources & evidence
- ORD record
- ord-3b4817c0fce24b5d91945e428deebbc4
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579897B2
Reaction notes
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