HCID 53916534, compound → HCID 19853671, compound

HRID 1650355Notes

Reaction equation

HRID 1650355 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F: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]([F: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 53916534HCID 53916534, compound

Product 1

HCID 19853671HCID 19853671, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 9.342 g (41.854 mM) of methyl 4-(2-amino-5-fluorophenyl)-4-oxo-2-butenoate in 200 ml of dioxane is hydrogenated in the presence of 10% of Pd-C at room temperature under atmospheric pressure. The reaction mixture is concentrated after removal of the catalyst. The resulting residue is chromatographed on a column of silica gel (463 g), eluting with toluene-ethyl acetate (19:1 v/v) to give 8.47 g of methyl 4-(2-amino-5-fluorophenyl)-4-oxobutyrate as orange crystals. Recrystallization from CH2Cl2 -Et2O-n-hexane gives 7.615 g (Yield: 80.8%) of the objective compound melting at 102°-103° C. as white needles.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customafter removal of the catalyst
  3. customThe resulting residue is chromatographed on a column of silica gel (463 g)
  4. washeluting with toluene-ethyl acetate (19:1 v/v)

Sources & evidence

ORD record
ord-bd10bcc4111747aeb18cc3121e48a42f
Source dataset
uspto-grants-1990_05
Patent number
US04923984

Reaction notes

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