Formaldehyde → Methyl N-methylanthranilate

Participants

Reaction Conditions

Reaction Steps

In a 2 L Parr pressure reactor was placed methyl anthranilate (302 g, 2.0 mol), ethyl acetate (700 mL), K-10 powder (30 g) 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 room temperature at an initial hydrogen pressure of 50 psig with continuous stirring. After hydrogen uptake had ceased (7 h), the mixture was filtered through filter-aid. The filtrate was dried and 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: 317 g (96% of theor.). GLC purity: 99.7%.

Provenance & Evidence