Hydrochloric Acid → HCID 90426657, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (21.31 mL, 256 mmol) was added to a solution of Example A2 (4.2 g, 10.1 mmol) in toluene (80 mL) and the reaction mixture was stirred at 110° C. for 1.5 h. The organic solvent was removed in vacuo and the remaining aqueous solution was diluted with water (50 mL), washed with toluene (2×20 mL), cooled in an ice bath, and adjusted to pH ˜12 with 50% NaOH (aq). The suspension was saturated with solid NaCl and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 3-((2-chloropyridin-4-yl)oxy)-6-hydrazinyl-2-methylpyridine (2.1 g, 83%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.24 (d, J=5.7 Hz, 1H), 7.50 (s, 1H), 7.30 (d, J=8.8 Hz, 1H), 6.88 (d, J=2.2 Hz, 1H), 6.85-6.84 (m, 1H), 6.63 (d, J=9.0 Hz, 1H), 4.13 (br s, 2H), 2.09 (s, 3H); MS (ESI) m/z: 251.1 (M+H+).

Provenance & Evidence