N-Methyl-N-(4-nitrophenyl)butyramide → HCID 28894251, compound

HRID 1983569Notes

Reaction equation

HRID 1983569 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[C:3](=[O:7])[CH2:4][CH2:5][CH3:6]>C(O)C.[Pd]>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([N:2]([CH3:1])[C:3](=[O:7])[CH2:4][CH2:5][CH3:6])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 68840696N-Methyl-N-(4-nitrophenyl)butyramide

Product 1

HCID 28894251HCID 28894251, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of the product of step 1 (1.08 g, 4.88 mmol) in ethanol (20 mL) was added 10% palladium on activated carbon (0.100 g). The reaction vessel was evacuated and backfilled with nitrogen several times. After a final evacuation the reaction vessel was backfilled with hydrogen. After 3.5 hours the hydrogen atmosphere was removed and the mixture was filtered through Celite and concentrated to afford 0.97 g (100%) of product as an amber gum: 1H NMR (CDCl3) δ 6.93 (d, J=8.6 Hz, 1H), 6.68 (d, J=8.6 Hz, 1H), 3.78 (br s, 2H), 3.20 (s, 3H), 2.04 (t, J=7.3 Hz, 2H 1.63-1.52 (m, 2H), 0.82 (t, J=7.4 Hz, 3H) ppm.

Workup

  1. customThe reaction vessel was evacuated
  2. customAfter 3.5 hours the hydrogen atmosphere was removed
  3. filtrationthe mixture was filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-24157eee65e740bcaf990564697808f2
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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