Ethyl 4-(2-nitrophenyl)-3-oxobutanoate → Ethyl 2-(1H-indol-2-yl)acetate

HRID 1095361Notes

Reaction equation

HRID 1095361 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([O-])=O>[Pd].C(O)C>[NH:1]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:10]=[C:11]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 10857922Ethyl 4-(2-nitrophenyl)-3-oxobutanoate

Product 1

HCID 11106442Ethyl 2-(1H-indol-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-(2-nitrophenyl)-3-oxobutanoate (17.04 g, 67.8 mmol), 10% palladium on carbon (3.6 g), and ethanol (280 mL) was placed under hydrogen pressure (50 psi, 3.4×105 Pa) on a Parr apparatus for 96 hours. The reaction mixture was filtered through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to provide crude ethyl 1H-indol-2-ylacetate.

Workup

  1. customfor 96 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dbb57773530b44718d2e39d4a90795f6
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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