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

HRID 1600754Notes

Reaction equation

HRID 1600754 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]>O1CCOCC1.O>[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

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 90496Indan-5-amine

Product 1

HCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5.2 g (39 mmol) of 5-aminoindan in 15 mL of dioxane kept in an ice-bath was added dropwise 8 mL (8.6 g, 84 mmol) of acetic anhydride. The solution was stirred at room temperature for 16 h. It was diluted with 70 mL of water. The mixture was filtered, washed with water, and dried to leave a gray solid 6.21 g (91%). 1H NMR (CDCl3), 2.069 (m, 2), 2.165 (s, 3), 2.879 (m, 4), 7.20 (mb, 1), 7.145 (s, 2), 7.441 (s, 1).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4daa832d236a489fba12862842b5993d
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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