Pyridine → HCID 86642356, compound

A mixture of 3-isobutoxyisonicotinic acid (2.2 g, 11.2 mmol) and oxalyl chloride (7 g, 55 mmol) in 25 mL of dichloromethane was stirred at room temperature for 1 h. The resulting solution was concentrated down under reduced pressure and the residue was re-dissolved in 50 mL of dichloromethane. To this solution were added N,O-dimethylhydroxyl-amine hydrochloride (4.5 g, 46.4 mmol) and pyridine (5 mL) at 0° C. The reaction was allowed to warm up to room temperature over 30 min period, and quenched with 2 mL of water. The resulting mixture was bacified with 1 mL 10% KOH solution (pH=10), the layers were separated, and the aqueous layer was washed twice with 20 mL portions of dichloromethane. The combined dichloromethane washes were dried over sodium sulfate, and concentrated down under reduced pressure, resulting in 1.8 g (67%) of 3-isobutoxy-N-methoxy-N-methylisonicotinamide. 1H-NMR (400 MHz, d6-DMSO): δ 8.46 (s, 1H), 8.25 (d, 1H), 7.45 (d, 1H), 3.96 (d, 2H), 3.43 (s, 3H), 2.76 (d, 3H), 2.05 (m, 1H), 0.94 (d, 6H). MS (EI) for C12H18N2O2: 239 (MH+).

1. concentrationThe resulting solution was concentrated down under reduced pressure
2. dissolutionthe residue was re-dissolved in 50 mL of dichloromethane
3. temperatureto warm up to room temperature over 30 min period
4. customquenched with 2 mL of water
5. customthe layers were separated
6. washthe aqueous layer was washed twice with 20 mL portions of dichloromethane
7. dry with materialThe combined dichloromethane washes were dried over sodium sulfate
8. concentrationconcentrated down under reduced pressure
9. customresulting in 1.8 g (67%) of 3-isobutoxy-N-methoxy-N-methylisonicotinamide

ORD record

ord-33d2add7dca44aebba956a0507c3870d

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324231B2