4-Methylmorpholine → 3-Fluoro-4-nitrobenzamide

Temperatur

0 °C

To a solution of 3-fluoro-4-nitrobenzoic acid, J. Am. Chem. Soc. 66, 1631-1632 (1944), (2.0 g, 10.81 mmol) in tetrahydrofuran (100 mL) at 0° C. was added 4-methyl morpholine (1.78 mL, 16.21 mmol), 1-hydroxybenzotriazole (2.18 g, 16.21 mmol), followed by 1-(3 dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.10 g, 16.21 mmol). The reaction was stirred for 1 hour at 0° C., then concentrated ammonium hydroxide was added (2.19 mL, 16.21 mmol). The reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was then diluted with ethyl acetate and washed with 5% citric acid (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a pale yellow powder. The powder was collected and washed with ether, followed by drying under reduced pressure to yield 3-fluoro-4-nitro-benzamide 1.22 g (69%). MS(APCI) m/z 183.0 (M−H). Anal. Calcd. for C7H5N2O3F1: C, 45.66; H, 2.74; N, 15.21. Found: C, 46.03; H, 2.75; N, 15.02.

1. temperatureto warm slowly to room temperature
2. stirringstirred overnight
3. washwashed with 5% citric acid (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto yield a pale yellow powder
8. customThe powder was collected
9. washwashed with ether
10. customby drying under reduced pressure

ORD-Eintrag

ord-7b4623b73dd04d73be91edd8796a705d

Quelldatensatz

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06875765B2