Ethanol → HCID 15533732, compound

HRID 1280332Notes

Reaction equation

HRID 1280332 reaction equation
[Cl-].[C:2]1([NH+:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C:17]1=O.C(O)C>O>[C:2]1([N:8]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:18]3[C:19]4[C:24]([CH2:16][C:17]2=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 119832-IndanoneHCID 45073535530-47-2

Product 1

HCID 15533732HCID 15533732, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 0.25 l bulb were placed 10 g (45 mmol) of N,N-diphenylhydrazinium chloride, 6.0 g (45 mmol) of 2-indanone and 50 ml of ethanol. The thus obtained mixture was heated at reflux for 4 hours and it was poured into water; the residual mixture was extracted with CH2Cl2 (150 ml) and the solvent was evaporated. The wanted compound was isolated by passing the obtained mixture through a column of silicagel, eluting with benzene/hexane=1:2. The resulting solution was evaporated and treated with 10 ml of hexane, obtaining the precipitation of crystals. Said crystals were separated, washed with hexane (10 ml) and finally dried, thus yielding 5.4 g of N-phenyl-5,6-dihydroindeno[2,1-b]indole (yield=45%).

Workup

  1. temperatureThe thus obtained mixture was heated
  2. temperatureat reflux for 4 hours
  3. extractionthe residual mixture was extracted with CH2Cl2 (150 ml)
  4. customthe solvent was evaporated
  5. customThe wanted compound was isolated
  6. washeluting with benzene/hexane=1:2
  7. customThe resulting solution was evaporated
  8. additiontreated with 10 ml of hexane
  9. customobtaining
  10. customthe precipitation of crystals
  11. customwere separated
  12. washwashed with hexane (10 ml)
  13. customfinally dried

Sources & evidence

ORD record
ord-53ee3f48c1d444c1b94b72dbf47b049b
Source dataset
uspto-grants-2002_09
Patent number
US06451724B1

Reaction notes

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