Phenyl-4-aminosalicylate

Chemical properties

WHITE POWDER

Originator

Pheny-Pas-Teb-Amin ,Purdue Frederick, US,1959

The Uses of Phenyl-4-aminosalicylate

Antibacterial(tuberculostatic).

The Uses of Phenyl-4-aminosalicylate

Phenyl 4-Aminosalicylate is a reactant in the synthesis of p-aminosalicylic ester imines with antitubercular activity.

Definition

ChEBI: 4-amino-2-hydroxybenzoic acid phenyl ester is a carbonyl compound.

Manufacturing Process

183 g of p-nitrosalicylic acid are dissolved in 564 g of phenol by heating to 140°C to 150°C on an oil bath. When all the p-nitrosalicylic acid is dissolved, 153 g of phosphorus oxychloride are run in, drop by drop, over a period of about 2 hours, while maintaining the temperature at about 150°C. The still warm mixture is run into 2 liters of water with agitation. The precipitate formed is filtered off, washed with water until phenol is removed and then dried.
There are thus obtained 250 g of 2-hydroxy-4-nitrophenylbenzoate which melts at 154°C to 155°C.
In a hydrogenation autoclave are introduced 92 g of 2-hydroxy-4nitrophenylbenzoate preceded by 200 cc of ethyl acetate; Raney nickel, obtained from 30 g of alloy, is added with 300 cc of ethyl acetate. Hydrogenation under pressure (100 to 120 kg) at ordinary temperature is carried out during a period of about 12 hours. The nickel is filtered off and the ethyl acetate is removed by distillation on the water bath under a vacuum of 300 mm. There is thus obtained 80 g of crude damp 2-hydroxy-4amnophenylbenzoate which after recrystallization from isopropyl alcohol melts at 153°C.

brand name

Pheny-Pas-Tebamin (Purdue Frederick).

Therapeutic Function

Antibacterial (tuberculostatic)

Metabolism

Not Available

Purification Methods

Crystallise the ester from EtOH (m 155o, also 149-150.5o), aqueous EtOH (m 147-149o), or isopropanol. It is tuberculostatic.[Beilstein 13 IV 1979.]