1-Indanone → Indeno(1,2-b)indole

HRID 2264848

Reaction equation

HRID 2264848 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>CCO.Cl>[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 2

HCID 67351-IndanoneHCID 125044-Methylphenylhydrazine monohydrochloride

Product 1

HCID 12963293Indeno(1,2-b)indole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

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

Workup

  1. temperatureare 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-e2d75bf28a83454989869f5ace82f047
Source dataset
uspto-grants-2010_12
Patent number
US07855255B2

Linked notes

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