Isopropanol → HCID 14973176, compound

HRID 1581733Notes

Reaction equation

HRID 1581733 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.C(O)(C)C.Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24]N)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:21](=[CH:22][CH:23]=1)[NH:24][C:2]1[CH2:3][C:4]3[C:9]([C:1]2=1)=[CH:8][CH:7]=[CH:6][CH:5]=3

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 119832-IndanoneHCID 516892Sodium BicarbonateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 14973176HCID 14973176, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

8.21 g of 2-indanone (Aldrich, 98%, Mw=132.16, 60.88 mmol), 40 mL of isopropanol, 10.84 g of p-methoxyphenylhydrazin hydrochloride (Aldrich, 98%, Mw=174.63, 60.83 mmol) were charged at room temperature in a 250 mL flask equipped with magnetic stirrer. The slurry was brought to reflux (82° C.), (a black slurry was obtained), and kept at reflux for 1 hour. The dark brown viscous suspension was then cooled to room temperature; 200 mL of water saturated with NaHCO3 were added into the reactor (final pH ca. 7.5-8), the resulting mixture was filtered and the residue washed with plenty of water. The dark green solid on the filter was dried in vacuo at 70° C. for 4 hours (14 g, 98.9% pure by GC, 96.7% yield of pure product).

Workup

  1. customequipped with magnetic stirrer
  2. custom(a black slurry was obtained), and
  3. temperatureat reflux for 1 hour
  4. temperatureThe dark brown viscous suspension was then cooled to room temperature
  5. filtrationwas filtered
  6. washthe residue washed with plenty of water

Sources & evidence

ORD record
ord-8afd3cf780cb4b90a25c578defd87253
Source dataset
uspto-grants-2004_05
Patent number
US06730754B2

Reaction notes

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