Phenylhydrazine → 5,10-Dihydroindeno[1,2-b]indole

HRID 1897537Notes

Reaction equation

HRID 1897537 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C.C(O)(=O)C>[CH:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH2:1][C:2]1[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:17][C:3]=12

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 119832-Indanone

Product 1

HCID 975985,10-Dihydroindeno[1,2-b]indole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A modified version of the method reported by Okamoto, et al. was employed. Okamoto, T. A.; Kobayashi, S. M.; Yamamoto, H. N., DE1952019, 1970. To a solution of 2-indanone (16.3 g, 123 mmol) in ethanol (80 mL) was added phenyl hydrazine (12.1 mL, 123 mmol) followed by acetic acid (12 drops) at room temperature. While stirring, the solution was warmed to reflux (oil bath at 85° C.) for 15 minutes at which point it was removed from the oil bath and allowed to cool to room temperature. Light yellow needle-like crystals precipitated from the solution. Upon cooling to room temperature, the solution was cooled to 0° C. for 30 minutes. The crystals were filtered via vacuum filtration and used without further purification.

Workup

  1. temperaturethe solution was warmed
  2. customwas removed from the oil bath
  3. temperatureto cool to room temperature
  4. customLight yellow needle-like crystals precipitated from the solution
  5. temperatureUpon cooling to room temperature
  6. temperaturethe solution was cooled to 0° C. for 30 minutes
  7. filtrationThe crystals were filtered via vacuum filtration
  8. customused without further purification

Sources & evidence

ORD record
ord-024396fb633f481f9298eb974539b4ae
Source dataset
uspto-grants-2013_08
Patent number
US08519122B2

Reaction notes

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