HCID 54022472, compound → HCID 14726176, compound

HRID 1650353Notes

Reaction equation

HRID 1650353 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13]>O1CCOCC1.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 54022472HCID 54022472, compound

Product 1

HCID 14726176HCID 14726176, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.435 g (18.506 mM) of methyl 4-(2-amino-5-chlorophenyl)-4-oxo-2-butenoate in 118 ml of dioxane is hydrogenated in the presence of 887 mg of 10% Pd-C under ordinaly pressure at room temperature. The mixture is concentrated after removal of the catalyst. The resulting residue is chromatographed on a column of silica gel (220 g), eluting with toluene-ethyl acetate (49:1-30:1 v/v) to give 3.877 g (Yield: 86.7%) of methyl 4-(2-amino-5-chlorophenyl)-4-oxobutyrate. This is recrystallized from CH2Cl2 -Et2O-n-hexane to give light yellow scaly prisms melting at 78°-79° C.

Workup

  1. concentrationThe mixture is concentrated
  2. customafter removal of the catalyst
  3. customThe resulting residue is chromatographed on a column of silica gel (220 g)
  4. washeluting with toluene-ethyl acetate (49:1-30:1 v/v)

Sources & evidence

ORD record
ord-7dbcab708f8b45fc83f8554b084b5a22
Source dataset
uspto-grants-1990_05
Patent number
US04923984

Reaction notes

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