Water → HCID 68603530, compound

Participants

Reaction Conditions

Reaction Steps

Methyl lithium (4.6 mL, 7.4 mmol, 1.6M in Et2O, Aldrich) was added dropwise to a solution of 3-isobutoxy-N-methoxy-N-methylisonicotinamide (0.88 g, 3.7 mmol) in 15 mL of THF at 0° C. The reaction mixture was allowed to stir at 0° C. for an additional 1 h. To the resulting mixture were added 1 mL of water and 2 drops of conc HCl. The layers were separated and the aqueous layer was washed twice with 20 mL portions of Et2O. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The product was purified by SiO2 flash chromatography (50:50 hexanes/ethyl acetate) to 450 mg (63%) of the title compound. 1H-NMR (400 MHz, d6-DMSO): δ 8.54 (s, 1H), 8.27 (d, 1H), 7.41 (d, 1H), 4.01 (d, 2H), 2.55 (s, 3H), 2.06 (m, 1H), 0.99 (d, 6H). MS (EI) for C12H18N2O2: 194 (MH+).

Provenance & Evidence