Description
4-(Methylamino) benzoic acid is an important intermediate for production of pharmaceutical products, dyes, flavors and preservatives.
Chemical Properties
white to beige powder
Uses
4-(Methylamino)benzoic acid important for the preparation of other pharmaceutical products, dyes, flavors, and preservatives. .For the preparation of medicines and other fine chemicals.
Definition
ChEBI: N-Methyl-4-aminobenzoate is an aminobenzoic acid.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
A mixture of 4-bromobenzoic acid (10 mmol), aqueous methylamine (5.4 mL, 5 equiv.), copper powder (0.032 g, 5 mol%), and a stirring bar was sealed in a dry reaction flask in a 30 ml threaded tube. The reaction mixture was stirred electromagnetically in an oil bath at 100C to dissolve the copper powder. After completion of the reaction (12 h), the reaction mixture was cooled to room temperature. The aromatic amine was extracted by adding ethyl acetate (20 ml) and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (3 10 mL) and all the organic layers were combined and dried with anhydrous sodium sulfate. The precipitate in the reaction mixture was removed by filtration and the resulting filtrate was concentrated under reduced pressure to remove the solvent, and finally the resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate) to obtain the target product molecule, 4-methylaminobenzoic acid.
References
https://www.alfa.com/en/catalog/A12426/
