HCID 178498360, compound → Halauxifen-methyl

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Reaction Steps

A magnetically stirred solution of 6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-[(E)-methanesulfonyloximino]-3-chloro-1,4,5,6-tetrahydropyridine-2-carboxylic acid methyl ester (29, 0.441 g (0.001 mol) in glacial acetic acid (2 mL) was warmed to 90° C. for 4 h. After removing the solvent on the rotary evaporator, the residue was dissolved in CH2Cl2 (25 mL) and was washed with saturated solutions of NaHCO3 and NaCl. After drying (MgSO4), solvent removal gave 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid methyl ester (39; 0.332 g, 96%; 93% pure by GC and 1H NMR spectroscopy) as a white solid: mp 141-143° C. 1H NMR (400 MHz, CDCl3) δ 7.65 (dd, J=8.6, 7.8 Hz, 1H), 7.23 (dd, J=8.7, 1.8 Hz, 1H), 7.18 (d, J=1.7 Hz, 1H), 4.85 (s, 2H), 4.00 (s, 3H), 3.97 (d, J=0.9 Hz, 3H). HRMS-ESI (m/z): calcd for C14H11Cl2FN2O3, 344.013. found, 344.013.

Provenance & Evidence