1-Indanone → Indeno(1,2-b)indole

HRID 2415397Notes

Reaction equation

HRID 2415397 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) is 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. temperatureis 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-9087924a72324276bd6ec0864f891209
Source dataset
uspto-grants-2004_11
Patent number
US06818713B1

Reaction notes

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