Indan-5-amine → N-(2,3-Dihydro-1H-inden-5-yl)acetamide

HRID 2084551Notes

Reaction equation

HRID 2084551 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[NH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2>C(OC(=O)C)(=O)C>[CH2:12]1[C:13]2[C:9](=[CH:8][C:7]([NH:6][C:1](=[O:4])[CH3:2])=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 90496Indan-5-amineHCID 517045Sodium Acetate

Product 1

HCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 70 ml of acetic anhydride and 15 g of sodium acetate is added dropwise, with stirring, to 50 g of-5-aminoindane. At the end of the exothermic reaction, the solution is heated at 100° C. for one hour. The solution is then poured into 500 g of ice; a precipitate is observed to form, which is collected by filtration and taken up in 400 ml of ethyl acetate. The solution is washed with 2×250 ml of water, 2×200 ml of a 20% sodium hydrogen carbonate solution, dried over Na2SO4 and concentrated in vacuo. The title compound is obtained in the form of a yellow solid.

Workup

  1. additionis added dropwise
  2. customAt the end of the exothermic reaction
  3. customto form
  4. filtrationwhich is collected by filtration
  5. washThe solution is washed with 2×250 ml of water, 2×200 ml of a 20% sodium hydrogen carbonate solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7623dc5cdbff4ee6b6cec93fd6ab2296
Source dataset
uspto-grants-2004_04
Patent number
US06716852B2

Reaction notes

Loading…