Dimethylformamide → 5-Fluoro-2-nitrobenzamide

Temperature

5 °C

Into a 1-L 3-necked round-bottom flask, was placed 5-fluoro-2-nitrobenzoic acid (25 g, 135.06 mmol, 1.00 equiv), dichloromethane (400 mL) and N,N-dimethylformamide (0.1 g). This was followed by the addition of (COCl)2 (30 g) dropwise with stirring at 0-10° C. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was dissolved in 200 mL of dichloromethane. To this was added ammonia (400 mL) dropwise with stirring at 0-10° C. The resulting solution was stirred for 2 h at room temperature. The solids were collected by filtration. This resulted in 20 g (80%) of 5-fluoro-2-nitrobenzamide as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 7.71 (s, 1H), 7.81 (s, 1H), 8.00 (s, 1H).

1. customInto a 1-L 3-necked round-bottom flask, was placed
2. stirringThe resulting solution was stirred overnight at room temperature
3. concentrationThe resulting mixture was concentrated under vacuum
4. dissolutionThe residue was dissolved in 200 mL of dichloromethane
5. additionTo this was added ammonia (400 mL) dropwise
6. stirringwith stirring at 0-10° C
7. stirringThe resulting solution was stirred for 2 h at room temperature
8. filtrationThe solids were collected by filtration
9. customThis resulted in 20 g (80%) of 5-fluoro-2-nitrobenzamide as a yellow solid

ORD record

ord-ee1f5850d4ee4b479d29d581121589bf

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193707B2