Hydrazine hydrate (1:1) → HCID 66788042, compound

HRID 1623547Notes

Reaction equation

HRID 1623547 reaction equation
[CH:1]1([C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[C:6](=O)[C:7](=[O:14])[N:8]3[CH3:13])[CH2:3][CH2:2]1.O.NN>ClCCl.O>[CH:1]1([C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[CH2:6][C:7](=[O:14])[N:8]3[CH3:13])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66788680HCID 66788680, compound

Product 1

HCID 66788042HCID 66788042, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

4-Cyclopropyl-1-methyl-1H-indole-2,3-dione (1.0 g, 4.2 mmol) was treated with hydrazine hydrate (7.0 mL, 225 mmol). The reaction was heated to 130° C. and stirred for 4 hours, at which time the reaction temperature was elevated to 150° C. for another 1.5 hours. The reaction was then placed at room temperature and cooled by the addition of ice. Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated. The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) ink 188.4 (M+H)+.

Workup

  1. waitwas elevated to 150° C. for another 1.5 hours
  2. customwas then placed at room temperature
  3. temperaturecooled by the addition of ice
  4. temperatureOnce the reaction was cooled to room temperature it
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted an additional two times with dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%)

Sources & evidence

ORD record
ord-c74f4ba399b942d4bda3719782598274
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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