Acetic Acid → Methyl N-methylanthranilate

In a 250 mL Parr shaking glass pressure reactor was placed methyl anthranilate (15.1 g, 0.10 mol), ethanol (70 mL), glacial acetic acid (6 g, 0.1 mol) and Raney nickel catalyst (2.1 g). To this cooled mixture at 5° C. was added 37% formaldehyde solution (8 mL, 0.10 mol). The mixture was then hydrogenated at 25° C. at an initial hydrogen pressure of 50 psig with continuous stirring. After hydrogen uptake had ceased (6 h), the mixture was filtered through filter-aid. The filtrate was washed to neutrality with saturated NaHCO3 (2×100 mL), and the layers were separated. The organic layer was washed with saturated NaCl (100 mL) and dried. The solvent was evaporated at reduced pressure. The residue was distilled to provide methyl N-methylanthranilate, b12.0 130°-133° C. as a colorless liquid. Yield: 14 g (85% of theor.). GLC purity: 98.5%.

1. custom(6 h)
2. filtrationthe mixture was filtered
3. filtrationthrough filter-aid
4. washThe filtrate was washed to neutrality with saturated NaHCO3 (2×100 mL)
5. customthe layers were separated
6. washThe organic layer was washed with saturated NaCl (100 mL)
7. customdried
8. customThe solvent was evaporated at reduced pressure
9. distillationThe residue was distilled

ORD record

ord-c411dc92bfda4425abaa845b8b663bb1

Source dataset

uspto-grants-1986_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04633009