Dimethylformamide → 4-Diisopropylaminomethyl-2-methoxybenzoic acid

Temperature

80 °C

A mixture of methyl 4-bromomethyl-2-methoxybenzoate (2.59 g), diisopropylamine (3.92 ml), potassium carbonate (1.38 g) and dimethylformamide (30 ml) was stirred at 80° C. for 2 hours, to which was added water and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was dissolved in THF-EtOH (1:1, 30 ml), to which was added 1 N sodium hydroxide solution (15 ml) and the solution was stirred at 80° C. for 20 minutes. To the solution was added water and the solution was washed with ether, made acidic with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was dissolved in THF and insoluble materials were filtered off. The filtrate was concentrated and crystallized with isopropylether to give the title compound (0.3 g).

1. extractionextracted with ethyl acetate
2. washThe extract was washed with water
3. dry with materialdried (MgSO4)
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in THF-EtOH (1:1, 30 ml), to which
6. additionwas added 1 N sodium hydroxide solution (15 ml)
7. stirringthe solution was stirred at 80° C. for 20 minutes
8. additionTo the solution was added water
9. washthe solution was washed with ether
10. extractionextracted with ethyl acetate
11. washThe extract was washed with water
12. dry with materialdried (MgSO4)
13. concentrationconcentrated
14. dissolutionThe residue was dissolved in THF
15. filtrationinsoluble materials were filtered off
16. concentrationThe filtrate was concentrated
17. customcrystallized with isopropylether

ORD record

ord-b464e2cc6f074b8baa0ad6ba5ad18a7a

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06359134B1