Hydrochloric Acid → 5-Methylindolin-2-one
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.NN.Cl>C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated to 140-160° C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water, and acidified to pH 2 with 6 N hydrochloric acid. After standing at room temperature for 2 days, the precipitate was collected by vacuum filtration, washed with water, and dried under vacuum to give 6.5 g (47%) of 5-methyl-2-oxindole.
Workup
- filtrationthe precipitate was collected by vacuum filtration
- washwashed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-87c94434fa3d4c069c16f4dc7bf9e816
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855730B2
Reaction notes
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