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

HRID 1857427Notes

Reaction equation

HRID 1857427 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-fe89eececfd94e938b30c20885b13da8
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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