Hydrochloric Acid → 1-ethyl-5-methyl-1,3-dihydro-2H-indol-2-one

HRID 421642Notes

Reaction equation

HRID 421642 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5](=O)[C:4]1=[O:14])[CH3:2].O.NN.Cl>CCOC(C)=O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 24713051-ethyl-5-methyl-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 112753291-ethyl-5-methyl-1,3-dihydro-2H-indol-2-oneYield 72.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-ethyl-5-methyl-1H-indole-2,3-dione (ix-a, 1.53 g, 8.09 mmol) and hydrazine monohydrate (30 mL, 618 mmol) was heated to 110° C. After 5 h, the reaction was cooled to RT and conc. HCl was added to adjust the reaction mixture to approximately pH 3. The mixture was stirred overnight, and poured into a separatory funnel containing EtOAc (150 mL). The mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (2×150 mL) and the combined organic layers were dried, filtered and concentrated to give 1-ethyl-5-methyl-1,3-dihydro-2H-indol-2-one (i-a, 1.03 g, 72.5%). NH4OAc QC conditions. DAD Retention time=1.48 min. M+H=176.

Workup

  1. temperaturethe reaction was cooled to RT
  2. additionpoured into a separatory funnel
  3. stirringThe mixture was shaken
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  6. customthe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-296693fb72a64cee99050775a71628d4
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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