1-Indanone → Indeno(1,2-b)indole

HRID 1609887

Reaction equation

HRID 1609887 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>C(O)C.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 ethanol (350 mL) and aqueous HCl (12 N, 18 mL) are heated to reflux for 90 minutes. The mixture is cooled and filtered, and the solid is washed with ethanol (600 mL) followed by 20% aqueous ethanol (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 minutes
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washthe solid is washed with ethanol (600 mL)
  6. customThe off-white solid is dried under vacuum (36.5 g, 72%)

Sources & evidence

ORD record
ord-82ddc71cd753491c8dcd622bab0152f9
Source dataset
uspto-grants-2006_01
Patent number
US06982305B2

Linked notes

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