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

HRID 751034

Reaction equation

HRID 751034 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2)([O-])=O.[CH3:13][C:14](OC(C)=O)=[O:15]>CO.N1C=CC=CC=1.[Pd]>[CH2:8]1[C:9]2[C:5](=[C:4]([NH:1][C:14](=[O:15])[CH3:13])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 2535784-Nitroindan

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A suspension of commercially available 4-nitroindane (10 g, 61.3 mmol) and 10% Pd/C (1 g) in MeOH (200 mL) was stirred vigorously under an atmosphere of hydrogen overnight at rt. The reaction was filtered through a pad of Celite® and concentrated, and residual solvent was removed by combining the reaction with toluene followed by evaporation. The crude reaction was taken up in pyridine (100 mL), and Ac2O (20 mL) was added and the reaction stirred for 16 h at rt. The reaction was evaporated and the crude product was purified by flash chromatography (5% MeOH in EtOAc/hexane(1:1) to give the title compound (9.12 g).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated
  3. customresidual solvent was removed
  4. customthe reaction with toluene
  5. customfollowed by evaporation
  6. customThe crude reaction
  7. stirringthe reaction stirred for 16 h at rt
  8. customThe reaction was evaporated
  9. customthe crude product was purified by flash chromatography (5% MeOH in EtOAc/hexane(1:1)

Sources & evidence

ORD record
ord-c4d0478f87594fe89b46f48e7df6cb22
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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