Acetonitrile → 4-Aminobenzoic Acid

HRID 266027Notes

Reaction equation

HRID 266027 reaction equation
ClC(=C(Cl)Cl)C([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(#N)C>CO>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 62657Potassium Phosphate, Tribasic2×HCID 19032249N-Trichloroacryloyl-p-aminobenzoic acid

Product 1

HCID 9784-Aminobenzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Trichloroacryloyl-p-aminobenzoic acid (440 μg) was dissolved in 1 mL of methanol, and 100 μL of this solution was added to 300 μL of potassium phosphate buffer (0.1 M, pH 8). In the same way a solution of p-aminobenzoic acid was prepared. Both solutions were analyzed by HPLC (C18-silica column, 0.01 M potassium phosphate buffer pH 4.5 initially, then 0 to 38% acetonitrile over 29 minutes. This gave a retention time of 6.8 min for p-aminobenzoic acid and 26 min for the product. The solutions were kept at room temperature. Analysis by HPLC demonstrated that the N-trichloroacryloyl-p-aminobenzoic acid was stable at least for four days. By this last day the solution of the p-aminobenzoic acid had discolored and additional peaks were seen.

Workup

  1. customIn the same way a solution of p-aminobenzoic acid was prepared

Sources & evidence

ORD record
ord-3e53379146534db49b785720eb59b4d2
Source dataset
uspto-grants-1997_07
Patent number
US05650270

Reaction notes

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