Hydrochloric Acid → 5-Methylindolin-2-one

HRID 24545

Reaction equation

HRID 24545 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]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 118405-MethylisatinHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 53257165-Methylindolin-2-oneYield 47.5%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

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

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-87c94434fa3d4c069c16f4dc7bf9e816
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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