Isopropanol → 5,6-Dihydroindeno[2,1-b]indole

HRID 1581735Notes

Reaction equation

HRID 1581735 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.Cl.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(O)C.C([O-])(O)=O.[Na+]>O>[CH:14]1[CH:15]=[CH:16][CH:17]=[C:12]2[C:13]=1[C:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C:2]=1[NH:18]2

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 119832-IndanoneHCID 60962Phenylhydrazine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 131294105,6-Dihydroindeno[2,1-b]indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a 1-L flask were charged 36.55 g of 2-indanone (Aldrich, Mw=−132.16, 276.6 mmol), 40.00 g of phenyl-hydrazine hydrochloride (Aldrich, 99%, Mw=144.61, 276.6 mmol) and 0.3 L of i-PrOH. The suspension was warmed to 80° C. in about 30 minutes and the slurry changed color from yellow to dark brown under stirring. The reaction mixture was stirred at 80° C. for 1.5 hours and then was cooled to room temperature in about 30 minutes. The slurry was siphoned into 1.0 L of water containing 34.85 g of NaHCO3, thus obtaining a fine dispersion of a green product (no heat evolution was observed). The slurry was then filtered on a G4 frit, washed with water, dried in air under moderate vacuum for 24 h until to achieve constant weight.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 1.5 hours
  2. temperaturewas cooled to room temperature in about 30 minutes
  3. customthus obtaining a fine dispersion of a green product (no heat evolution
  4. filtrationThe slurry was then filtered on a G4 frit
  5. washwashed with water
  6. customdried in air under moderate vacuum for 24 h until

Sources & evidence

ORD record
ord-854b7ba5fe4c4930b3d0e1dfd3a4bab2
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

Loading…