Ethyl-12-(m-nitrophenyl)-11-dodecenoate → Ethyl-12-(m-aminophenyl)-dodecanoate

HRID 2226288Notes

Reaction equation

HRID 2226288 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH3:2]

Participants

4

Reactant 1

HCID 53714556Ethyl-12-(m-nitrophenyl)-11-dodecenoate

Product 1

HCID 14584161Ethyl-12-(m-aminophenyl)-dodecanoateYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl-12-(m-nitrophenyl)-11-dodecenoate (9.76 g, 28.1 mmol was dissolved in ethyl acetate (55 ml). The solution was hydrogenated over 5% Pd/C (0.346 g) at room temperature and at an initial pressure of 45 psi for four hours. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to yield an oily residue. The crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1) to yield the reduced compound 5, ethyl-12-(m-aminophenyl)-dodecanoate (8.75 g, 97.5% yield).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customto yield an oily residue
  4. customThe crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1)

Sources & evidence

ORD record
ord-fe1c7b133eb34c13ba00377209685fea
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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