(RS)-ethyl 2-(4-nitrophenyl)-heptanoate → (RS)-ethyl 2-(4-aminophenyl)-heptanoate

HRID 394940Notes

Reaction equation

HRID 394940 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 86584487(RS)-ethyl 2-(4-nitrophenyl)-heptanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 86584488(RS)-ethyl 2-(4-aminophenyl)-heptanoateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

12 g of (RS)-ethyl 2-(4-nitrophenyl)-heptanoate dissolved in 100 ml of ethanol was treated with 2.4 g of 10% palladium on carbon. The mixture was stirred at room temperature for 18 hours under 40 psi of hydrogen. The mixture was filtered on a pad of Celite and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes), yielding 10.4 g of a pale yellow oil. 1H NMR (CDCl3): 7.10 (d, J=8.4 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 4.20-4.00 (m, 2H), 3.61 (br. s, 2H), 3.40 (t, J=7.7 Hz, 1H), 2.05-1.90 (m, 1H), 1.75-1.60 (m, 1H), 1.30-1.15 (m, 6H), 1.20 (t, J=7.2 Hz, 3H), 0.85 (t, J=6.7 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered on a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2d774b5751ca4c0a80f426e4c0908930
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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