HCID 67206429, compound → HCID 58288181, compound

HRID 1476107Notes

Reaction equation

HRID 1476107 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9](=[CH:15][CH3:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].NC1C=C(C(CC)=CC(OC)=O)C=CC=1Cl>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH3:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 67206429HCID 67206429, compoundHCID 67207565HCID 67207565, compound

Product 1

HCID 58288181HCID 58288181, compoundYield 121.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.05 g (12.7 mmol) of methyl 3-(3-amino-4-chlorophenyl)pent-3-enoate and 0.85 g (3.55 mmol) of methyl 3-(3-amino-4-chlorophenyl)pent-2-enoate were dissolved together in 500 ml of ethyl acetate, 346 mg (0.325 mmol) of palladium on carbon (10%) were added and the mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure overnight. The reaction mixture was then filtered off through celite, the residue was washed with ethyl acetate and the filtrate was concentrated. Drying of the residue under high vacuum gave 3.73 g of the target product (94.8% of theory).

Workup

  1. filtrationThe reaction mixture was then filtered off through celite
  2. washthe residue was washed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customDrying of the residue under high vacuum

Sources & evidence

ORD record
ord-baa5ef0811aa4d0ca30b8d17715b52d4
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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