Hydrochloric Acid → Methyl 4-amino-3-methylbenzoate

To a 500 mL round bottomed flask equipped with a stirring bar, reflux condenser and a drying tube was added 3-methyl-4-aminobenzoic acid (8.00 g, 52.92 mmol) and anhydrous methanol (300 mL). This solution was saturated with anhydrous HCl gas and the mixture was stirred at ambient temperature for 26 h. The methanol and HCl were removed in vacuo and the solid product was suspended in 400 mL of EtOAc. This mixture was made basic by careful addition of aqueous NaHCO3 solution. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give methyl 3-methyl-4-aminobenzoate as a yellow solid.

1. customTo a 500 mL round bottomed flask equipped with a stirring bar
2. temperaturereflux condenser and a drying tube
3. customThe methanol and HCl were removed in vacuo
4. additionThis mixture was made basic by careful addition of aqueous NaHCO3 solution
5. customThe layers were separated
6. washthe organic phase was washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-fd4a3ec5f3904343a55f541d8f05b36b

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05854245