Hydrochloric Acid → Indeno(1,2-b)indole

HRID 552054

Reaction equation

HRID 552054 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[C:12]1(C)[CH:17]=[CH:16][C:15]([NH:18]N)=[CH:14][CH:13]=1.Cl>CCO>[CH:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[C:2]1[C:16]3[CH:17]=[CH:12][CH:13]=[CH:14][C:15]=3[N:18]=[C:1]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 125044-Methylphenylhydrazine monohydrochloride

Product 1

HCID 12963293Indeno(1,2-b)indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Indanone (30.6 g, 232 mmol), p-tolylhydrazine hydrochloride (37.0 g, 233 mmol) in EtOH (350 mL), and aqueous HCl (12 N, 18 mL) are mixed and the mixture is heated to reflux for 90 min. The mixture is cooled and filtered, and the solid is washed with EtOH (600 mL) and then by 20% aqueous EtOH (400 mL), and finally by hexane (200 mL). The off-white solid is dried under vacuum (36.5 g, 72%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 90 min
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washthe solid is washed with EtOH (600 mL)
  6. customThe off-white solid is dried under vacuum (36.5 g, 72%)

Sources & evidence

ORD record
ord-1368952d651f4d989e6a5b58dd0bf366
Source dataset
uspto-grants-2011_05
Patent number
US07951743B2

Linked notes

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