Acetic Anhydride → N-(2,3-Dihydro-1H-inden-5-yl)acetamide

HRID 1710311Notes

Reaction equation

HRID 1710311 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(O)(=O)C>[C:11]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 90496Indan-5-amine

Product 1

HCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamideYield 84.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

33.3 g (0.25 mol) of 5-aminoindane (a product of Tokyo Chemical Industry Co. Ltd.) was dissolved in 250 ml of glacial acetic acid, the resulting solution was heated to 50° C., and 51.0 g (0.5 mol) of acetic anhydride was added dropwise thereto. After completion of the dropwise addition, the resulting solution was stirred for 4 hours. After completion of the reaction, the reaction liquid was poured in 1,500 ml of ice water while stirring. Crystals precipitated were filtered off, and washed with 1,000 ml of water. The crystals obtained were dried to obtain 37.06 g of 5-(N-acetylamino)indane (yield: 84.6%, melting point: 100.5 to 103.5° C.)

Workup

  1. additionAfter completion of the dropwise addition
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. stirringwhile stirring
  5. customCrystals precipitated
  6. filtrationwere filtered off
  7. washwashed with 1,000 ml of water
  8. customThe crystals obtained
  9. customwere dried

Sources & evidence

ORD record
ord-7573a06fde9e4be5af8da2e0a35cb8d9
Source dataset
uspto-grants-2010_09
Patent number
US07790342B2

Reaction notes

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