Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide → Heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide

HRID 47828Notes

Reaction equation

HRID 47828 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 86586370Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide

Product 1

HCID 86586371Heptanoic acid [2-(4-amino-phenyl)-ethyl]-amideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1H NMR (400 MHz, CDCl3) δ8.16 (d, 2H), 7.35 (d, 2H), 5.43 (s, 1H), 3.54 (m, 2H), 2.93 (t, 2H), 2.12 (t, 2H), 1.57 (m, 3H), 1.26 (m, 5H), 0.86 (t, 3H). 10% Palladium on carbon (380 mg, 10 wt %) was added to a solution of heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide (3.80 g, 13.6 mmol) and methanol (80 mL) in a Parr bottle and the resulting mixture hydrogenated at 55 psi for 4 h. The reaction mixture was filtered through a plug of Celite and the Celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 3.24 g (96%) of heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washthe Celite plug washed thoroughly with ethyl acetate
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-af1b1fd52dba47978b90a71681542d81
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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