Ethyl Acetate → 2,4-Dichloroaniline

HRID 1486959Notes

Reaction equation

HRID 1486959 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])N=1.[CH3:12]C(=O)OCC>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:12]=[C:4]([Cl:11])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 111232,4-DichloroanilineYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2,6-dichloro-3-nitropyridine (100 g, 0.518 mol) in acetic acid (1 L) was added iron powder (86.49 g, 1.555 mol) portion wise. The resulting reaction mixture was stirred at room temperature for 6 h. The completion of the reaction was confirmed by checking TLC system (PE/EA=8:2). The reaction mass was concentrated under high vacuum. The crude was dissolved in water (1 L) and EtOAc (2 L). While stirring, the pH of the aqueous solution was adjusted to 6.5 using powder Na2CO3. The mixture was filtered through CELITE® and the organic layer was separated, dried and concentrated to give 2,4-dichloroaniline (80 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14-7.2 (2H, m); 5.78 (2H, s).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mass was concentrated under high vacuum
  3. dissolutionThe crude was dissolved in water (1 L)
  4. stirringWhile stirring
  5. filtrationThe mixture was filtered through CELITE®
  6. customthe organic layer was separated
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ff347d8caf414597ad249884ca58ec58
Source dataset
uspto-grants-2016_08
Patent number
US09428504B2

Reaction notes

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