Hydrochloric Acid → 5-Methylindolin-2-one

HRID 1840473Notes

Reaction equation

HRID 1840473 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>>[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

4

Reactant 3

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

Product 1

HCID 53257165-Methylindolin-2-oneYield 47.5%

Procedure

A solution of 5-methylisatin (15.0 g) and hydrazine hydrate (60 mL) was heated to 140-160° C. for 4 hours. 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% yield) 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-6217b3d7bebe4ab2b7476f37330c17e3
Source dataset
uspto-grants-2004_01
Patent number
US06680335B2

Reaction notes

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