Dimethylformamide → HCID 57636432, compound

Temperature

2.5 °C

2-Fluoro-4-nitrobenzoic acid (1.002 g, 5.41 mmol) was dissolved in dichloromethane and cooled in an ice bath. DMF (0.1 mL) and oxalyl chloride (0.71 mL, 8.4 mmol) were added, and the reaction mixture was stirred at ice bath temperature (0-5° C.) for two houres. Dichloromethane (25 mL) was added, followed by isopropylamine (1.85 mL, 21.7 mmol). The ice bath was removed and the reaction mixture was stirred for 2.5 hours. The reaction mixture was washed with 25 mL of 10% aqueous NaOH solution, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (EtOAc/hexanes 0-33%) to give 1,015 g of 2-fluoro-N-isopropyl-4-nitro-benzamide.

1. temperaturecooled in an ice bath
2. customThe ice bath was removed
3. stirringthe reaction mixture was stirred for 2.5 hours
4. washThe reaction mixture was washed with 25 mL of 10% aqueous NaOH solution
5. customthe organic layer was separated
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was chromatographed through silica gel (EtOAc/hexanes 0-33%)

ORD record

ord-47a09d4dd6054093ab88fd5e1f913323

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517901B2