Acetic Anhydride → N-(2,3-Dihydro-1H-inden-4-yl)acetamide

HRID 2112080Notes

Reaction equation

HRID 2112080 reaction equation
[CH2:1]1[C:9]2[C:4](=[C:5]([NH2:10])[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[CH2:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11](=[O:13])[CH3:12])[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1225694-Aminoindan

Product 1

HCID 12683814N-(2,3-Dihydro-1H-inden-4-yl)acetamide

Conditions

Temperature
70 °C

Procedure

226 mg (1.7 mmol) indan-4-ylamine are combined with 5 ml acetic anhydride. The suspension is stirred for 16 h at 70° C. The resulting solution is stirred into 40 ml distilled water, adjusted to pH 7 with sodium carbonate and extracted three times with 30 ml of ethyl acetate. Then the organic phase is dried with MgSO4, the solvent is eliminated in vacuo and the crude product is purified by chromatography. The carrier used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (70:30).

Workup

  1. stirringThe resulting solution is stirred into 40 ml
  2. distillationdistilled water
  3. extractionextracted three times with 30 ml of ethyl acetate
  4. dry with materialThen the organic phase is dried with MgSO4
  5. customthe crude product is purified by chromatography
  6. additiona mixture of cyclohexane:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-b8671e18bac446599a3e141b16f5ffca
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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