2,4-Dichloro-3-ethenylbenzenamine → HCID 58977255, compound

HRID 1811530Notes

Reaction equation

HRID 1811530 reaction equation
[Cl:1][C:2]1[C:8]([CH:9]=[CH2:10])=[C:7]([Cl:11])[CH:6]=[CH:5][C:3]=1[NH2:4]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[C:8]([CH2:9][CH3:10])=[C:7]([Cl:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 688217902,4-Dichloro-3-ethenylbenzenamine

Product 1

HCID 58977255HCID 58977255, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloro-3-vinylaniline (4.9 g, 26 mmol) in EtOAc (60 mL) is added 10% Pd/C (0.50 g). The pressure flask is filled with H2 at 55 psi and shaken for 2 hrs. Excess H2 is removed and the mixture is filtered through a pad of celite. The solvent is removed and the resulting mixture is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-ethylaniline.

Workup

  1. additionThe pressure flask is filled with H2 at 55 psi
  2. customExcess H2 is removed
  3. filtrationthe mixture is filtered through a pad of celite
  4. customThe solvent is removed
  5. customthe resulting mixture is purified through a flash chromatographic column with a gradient of hexanes/ether

Sources & evidence

ORD record
ord-f327fcb615444f3ca43856d1f39ce846
Source dataset
uspto-grants-2013_01
Patent number
US08362294B2

Reaction notes

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