Triethylamine → 4-Fluoro-N-methoxy-N-methylbenzamide

To a mixture of 4-fluorobenzoic acid (5.0 grams (hereinafter “g”), 36 millimoles (hereinafter “mmol”)) and N,O-dimethylhydroxylamine hydrochloride (3.8 g, 39 mmol) in 200 mL of CH2Cl2 at 0° C. was added triethylamine (5.0 milliliters (hereinafter “mL”), 36 mmol). The solution was warmed to room temperature and 4-dimethylaminopyridine (0.2 g, 1.6 mmol) and 1-(dimethylaminopropyl)-3-ethylcarbodiimide (6.8 g, 36 mmol) were added. The resulting solution was stirred for 16 hours (hereinafter “h”). Next, the solution was diluted with 200 mL of ethyl acetate and washed with 100 mL of saturated NaHCO3, 50 mL of H2O, twice with 50 mL of 1N HCl, and 50 mL of H2O. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give a light yellow oil. The oil was purified by chromatography through a plug of silica gel with 50% ethyl acetate/hexane to give title compound as a light yellow oil (5.5 g, 85%). ES(+)MS m/e=184 (MH+)

1. washwashed with 100 mL of saturated NaHCO3, 50 mL of H2O, twice with 50 mL of 1N HCl, and 50 mL of H2O
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customto give a light yellow oil
6. customThe oil was purified by chromatography through a plug of silica gel with 50% ethyl acetate/hexane

ORD record

ord-e10df9b8fd174191917c170203f1a663

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610695B1