Ammonia → 2-(2,3-Dihydro-1H-inden-2-yl)acetamide

HRID 1654944Notes

Reaction equation

HRID 1654944 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([OH:13])=O.S(Cl)(Cl)=O.[NH3:18]>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([NH2:18])=[O:13]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Product 1

HCID 189215242-(2,3-Dihydro-1H-inden-2-yl)acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

35.3 g (0.20 mol) of (indan-2-yl)acetic acid was dissolved in 350 ml methylene chloride, to which was added 26.5 g (0.22 mol) of thionyl chloride and stirred for 4 hours at room temperature, followed by refluxing for further 1.5 hours. After cooled and condensed under reduced pressure, the obtained oily residue was dissolved in 100 ml ethyl acetate and added dropwise to 200 ml conc. aqueous ammonia while stirred vigorously under ice-cooling. After stirring for 20 minutes, the precipitates were collected by filtration and recrystallized from a solvent mixture of ethyl acetate and ethanol. 32.1 g of colorless crystal was obtained. Yield: 95%

Workup

  1. temperatureby refluxing for further 1.5 hours
  2. temperatureAfter cooled
  3. customcondensed under reduced pressure
  4. stirringwhile stirred vigorously under ice-
  5. temperaturecooling
  6. stirringAfter stirring for 20 minutes
  7. filtrationthe precipitates were collected by filtration
  8. customrecrystallized from a solvent mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-5ff212c096f64ae19fa957e1f804ab7e
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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