Ammonia → Benzenepropanamide, 2-(4-(acetylamino)-1-oxobutyl)-5-chloro-

HRID 1639382Notes

Reaction equation

HRID 1639382 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:11]=1[CH2:12][CH2:13][C:14](OC)=[O:15])=[O:9])(=[O:3])[CH3:2].[NH3:23]>CO>[CH3:2][C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:11]=1[CH2:12][CH2:13][C:14]([NH2:23])=[O:15])=[O:9])=[O:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19833136HCID 19833136, compound

Product 1

HCID 3078715Benzenepropanamide, 2-(4-(acetylamino)-1-oxobutyl)-5-chloro-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.15 g (0.025 mol) of methyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate are stirred at room temperature for 30 hours in 200 ml of a solution of ammonia in methanol. After concentration of the solution the residue is extracted with methylene chloride/water, dried with magnesium sulfate, the solvent is distilled in a vacuum. The residue is chromatographed on silica gel with chloroform-methanol (9:1). Recrystallization from methanol/ether yields 2-(4-acetamidobutyryl)-5-chlorohydrocinnamide as white crystals with melting point 149°-151°.

Workup

  1. extractionAfter concentration of the solution the residue is extracted with methylene chloride/water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe solvent is distilled in a vacuum
  4. customThe residue is chromatographed on silica gel with chloroform-methanol (9:1)
  5. customRecrystallization from methanol/ether

Sources & evidence

ORD record
ord-8b3af53366884fe59851edcd62e72fd4
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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