HCID 54328878, compound → Ethyl 4-(2-carbamoylanilino)butanoate

HRID 1464274Notes

Reaction equation

HRID 1464274 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][CH2:8][NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13])=[O:5])[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 54328878HCID 54328878, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13111329Ethyl 4-(2-carbamoylanilino)butanoateYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3-ethoxycarbonyl-2-propenylamino)benzamide (2.35 g) in methanol (50 ml) was added 10% palladium on carbon (230 mg). The mixture was stirred vigorously under 3 atmospheric pressure of hydrogen. After 2 hours, the catalyst was filtered off, and the solvent was evaporated. The residue was chromatographed on silica gel (40 g). Elution with a mixed solvent of ethyl acetate-hexane (1:1 V/V) gave 2-(3-ethoxycarbonylpropylamino)benzamide (1.95 g).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed on silica gel (40 g)
  4. washElution with a mixed solvent of ethyl acetate-hexane (1:1 V/V)

Sources & evidence

ORD record
ord-2f68476d51ef46c98fdbf9a5ed8b6612
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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