HCID 54472399, compound → Methyl 4-(2-aminophenyl)-4-oxobutanoate

HRID 1650357Notes

Reaction equation

HRID 1650357 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:15])[CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12]>CO.O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 1

HCID 54472399HCID 54472399, compound

Product 1

HCID 14726177Methyl 4-(2-aminophenyl)-4-oxobutanoateYield 76.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.87 g (23.73 mM) of methyl 4-(2-aminophenyl)-4-oxo-2-butenoate in 120 ml of methanol and 6 ml of water is hydrogenated in the presence of 974 mg of 10% Pd-C at room temperature under atmospheric pressure. After removal of the catalyst, the mixture is concentrated to give a residue, which is chromatographed on a column of silica gel (274 g), eluting with toluene-ethyl acetate (30:1-19:1 v/v) to give 3.746 g of methyl 4-(2-aminophenyl)-4-oxobutyrate as orange crystals. This is recrystallized from Et2O-n-hexane to give 3.162 g (Yield: 64.3%) melting at 50.0°-51.0° C. as yellow crystals.

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe mixture is concentrated
  3. customto give a residue, which
  4. customis chromatographed on a column of silica gel (274 g)
  5. washeluting with toluene-ethyl acetate (30:1-19:1 v/v)

Sources & evidence

ORD record
ord-d74df527a0bd43c8bec2f89bf339bddd
Source dataset
uspto-grants-1990_05
Patent number
US04923984

Reaction notes

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