Acetic Acid → 4-Methoxy-N-{2-[1-(pyridin-2-yl)ethyl]phenyl}benzamide

HRID 1579371Notes

Reaction equation

HRID 1579371 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[C:9]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:10]1[NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH3:8].C(O)(=O)C.O.[OH-].[NH4+]>[Pd].C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[CH:25]=[CH:24][CH:23]=[CH:22][C:10]=1[NH:11][C:12](=[O:21])[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[CH3:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 70563359HCID 70563359, compound

Product 1

HCID 205600374-Methoxy-N-{2-[1-(pyridin-2-yl)ethyl]phenyl}benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2'-[1-(2-Pyridyl)ethylidene]-p-anisanilide (6.0 g., 0.018 mole) is reduced in a Parr apparatus in 100 ml. of acetic acid employing 1.0 g. of 10% palladium on carbon catalyst. The catalyst is collected, the filtrate concentrated under reduced pressure and the residue thus obtained distributed between water and ethyl acetate. This mixture is made basic with concentrated ammonium hydroxide and the ethyl acetate extract separated, dried, and concentrated to provide 2'-1-(2-pyridyl)ethyl-p-anisanilide, m.p. 125°-126°C. (corr.), from aqueous ethanol.

Workup

  1. customThe catalyst is collected
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue thus obtained
  4. extractionthe ethyl acetate extract
  5. customseparated
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-417c4b5d49f64167a7fbdd2bc1c06aa5
Source dataset
uspto-grants-1976_01
Patent number
US03931195

Reaction notes

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