Water → 2,4,6-Trichloroaniline

HRID 67166Notes

Reaction equation

HRID 67166 reaction equation
O.C(NC1CC(=O)[N:8]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])N=1)(=O)C>C(O)C>[Cl:18][C:17]1[CH:16]=[C:15]([Cl:19])[CH:14]=[C:13]([Cl:20])[C:12]=1[NH2:8]

Participants

4

Reactant 2

HCID 962WaterHCID 4497701N-[5-oxo-1-(2,4,6-trichlorophenyl)-2-pyrazolin-3-yl]acetamide

Product 1

HCID 124712,4,6-TrichloroanilineYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The procedure was repeated using a mixture of 20% water and 80% ethanol as the solvent instead of the anhydrous ethanol used above. This time the yield of 3-acetamido-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one was very poor, i.e., only 8%, while a 57% yield of 2,4,6-trichloroaniline was obtained. This illustrates that, in contrast to the excellent yields produced in an organic medium, very poor yields are obtained when the rearrangement is run in an aqueous medium.

Sources & evidence

ORD record
ord-0241c10657e44f2dabb785f7ce737461
Source dataset
uspto-grants-1982_08
Patent number
US04345085

Reaction notes

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