Dichloromethane → HCID 58009889, compound

A round bottom flask was charged with 6-fluoro-4-methylnicotinic acid (1.13 g, 7.28 mmol, Frontier) and DCM (73 mL) to give a clear solution. Thionyl chloride (5.32 mL, 72.8 mmol) was added drop-wise and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in EtOAc (10 mL) and added drop-wise to a rapidly stirred mixture of EtOAc (40 mL) and concentrated aqueous NH4OH (36.9 ml, 947 mmol). The mixture was stirred for about 1 h, and the layers were separated. The aqueous layer was further extracted with EtOAc (50 mL) and the combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure to give 6-fluoro-4-methylnicotinamide (0.69 g, 61%) as white solid: LC/MS (Table 2, Method d) Rt=1.03 min; MS m/z 153 (M−H)−.

1. customto give a clear solution
2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
3. dissolutionthe residue was dissolved in EtOAc (10 mL)
4. additionadded drop-wise
5. stirringThe mixture was stirred for about 1 h
6. customthe layers were separated
7. extractionThe aqueous layer was further extracted with EtOAc (50 mL)
8. washthe combined extracts were washed with brine
9. dry with materialdried over anhydrous Na2SO4
10. filtrationfiltered
11. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-af43e711ef844cc4a4e3b7d2cdd25c2b

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2