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

HRID 441475Notes

Reaction equation

HRID 441475 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)=O)[CH3:2]>[Pd].C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[NH:15][C:10]2[C:9]([CH:8]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:2]

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 176Acetic AcidSolvent

Procedure

A sample of 12.0 gm (0.048M) of ethyl-γ-2-nitrophenylacetoacetate was dissolved in 200 cc. glacial acetic acid. Approximately 21/2 spatulas of 5% Pd/C was added to the solution and the compound was reduced on the Parr hydrogenator. Ethyl-2-indolylacetate was obtained as a dark orangy oily liquid after removal of catalyst and solvent.

Sources & evidence

ORD record
ord-156003c0cf24440b926e190e9cdcd425
Source dataset
uspto-grants-1977_08
Patent number
US04040832

Reaction notes

Loading…