Ethyl Acetate → 4-Aminoindan

HRID 1671629

Reaction equation

HRID 1671629 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.C(OCC)(=O)C>C(O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2535784-Nitroindan

Product 1

HCID 1225694-AminoindanYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

In a 500 mL Parr shaker vessel, 4-nitroindane (10 g, 61 mmol) was dissolved in 50 mL ethanol. A slurry of 10% Pd/C (1 g) in ethanol was added. The mixture was then placed on a Parr shaker under a hydrogen atmosphere (50 psi) for 1 hour, at which point t.l.c. (20% ethyl acetate in hexanes) showed that all the starting material had disappeared. To work up the reaction, the mixture was filtered twice through Celite, washing with a large amount of ethanol, and once through filter paper. The ethanol was evaporated under reduced pressure, and the crude product purified by flash chromatography over silica gel (10% ethyl acetate in hexanes) to give 8 as a viscous, faintly colored oil (7.04 g, 86% yield): 1H NMR (400 MHz, DMSO-D6) δ 1.95 (m, 2H) 2.61 (t, J=7.3 Hz, 2H) 2.76 (t, J=7.5 Hz, 2H) 4.77 (s, 2H) 6.36 (d, J=7.8 Hz, 1H) 6.42 (d, J=6.8 Hz, 1H) 6.80 (t, J=7.6 Hz, 1H).

Workup

  1. customfor 1 hour
  2. customthe reaction
  3. filtrationthe mixture was filtered twice through Celite
  4. washwashing with a large amount of ethanol
  5. filtrationonce through filter paper
  6. customThe ethanol was evaporated under reduced pressure
  7. customthe crude product purified by flash chromatography over silica gel (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bab299247af647cc87b99e792737d4ad
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Linked notes

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