Sodium Hydroxide → Sodium 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

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Reaction Steps

To a stirring suspension of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (4.12 g, 7.73 mmol) in methanol (100 mL) was added 1 N sodium hydroxide (7.73 mL, 7.73 mmol). The mixture was stirred for approximately 1 hour and then concentrated. Ether was added followed by a little water. After stirring the solid turned into a paste. The solvent was decanted and the paste triturated with ether and then dried on a rotary evaporator at 35° C. under vacuum for approximately 1.5 hours to afford sodium 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (4.24 g, 98%). 1H-NMR (400 MHz, DMSO-d6) δ 8.28-8.22 (m, 2H), 8.09-7.96 (m, 3H), 7.68 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.90 (d, J=9 Hz, 2H), 4.87 (s, 2H), 3.46 (septet, J=7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). LRMS (APCI) C29H21Cl2N2O4Na calculated: 533 (M+H)+, found: 533 (M+H)+.

Provenance & Evidence