Acetic Acid → Methyl N-methylanthranilate

Participants

Reaction Conditions

Reaction Steps

In a 2L Parr pressure reactor was placed methyl anthranilate (302 g, 2.0 mol), ethyl acetate (700 mL), glacial acetic acid (120 g, 2.0 mol), and 5% palladium on carbon catalyst (30 g). The mixture was cooled to 5° C. and 37% aqueous formaldehyde solution (160 mL, 2.12 mol) was added. The mixture was then hydrogenated at 25° C. at an initial hydrogen pressure of 50 psig with continuous stirring. After hydrogen uptake had ceased (12 h), the mixture was filtered through filter-aid. The filtrate was washed to neutrality with saturated NaHCO3 (3×300 mL) and the layers were separated. The organic layer was washed with saturated NaCl (400 mL), and dried. The solvent was evaporated at reduced pressure. The residue was distilled through a Vigreaux column (30×2 cm) to provide methyl N-methylanthranilate, b12.0 130°-132 ° C. as a colorless liquid. Yield: 300 g (91% of theor.). GLC purity: 97.3%.

Provenance & Evidence