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

HRID 1654778Notes

Reaction equation

HRID 1654778 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(Cl)Cl>[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 928.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-aminoindane (10.0 g, 7.5 mmol) in CH2Cl2 (100 mL) was added dropwise acetic anhydride (9.2 g, 9.0 mmol) over a period of 1.5 min. After further stirring for 30 min, the mixture was quenched with 1M aqueous NaOH (100 mL). The CH2Cd2 layer was separated, washed successively with 1M aqueous HCl, brine, and was then dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel, eluting with ethyl acetate:hexanes (1:1) afforded 12.2 g (85%) of the title compound as a light brown powder.

Workup

  1. customthe mixture was quenched with 1M aqueous NaOH (100 mL)
  2. customThe CH2Cd2 layer was separated
  3. washwashed successively with 1M aqueous HCl, brine
  4. dry with materialwas then dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel, eluting with ethyl acetate:hexanes (1:1)

Sources & evidence

ORD record
ord-66fe4a16287446b69189576cf144f8c7
Source dataset
uspto-grants-1995_04
Patent number
US05409944

Reaction notes

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