Sodium Hydroxide → 4-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalic acid

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Reaction Steps

A mixture of dimethyl 4-({[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)isophthalate (230 mg, 0.468 mmol), prepared in the previous step, and 1 N NaOH (2.81 mL, 2.81 mmol) in 30 mL of THF plus 20 mL of methanol plus 5 mL of water was refluxed under nitrogen for 7 h. The reaction was filtered, cooled to room temperature, acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure at 60° C. to give the title compound (204 mg, 94%) as a yellow solid, mp 289–291° C. Elemental Analysis for C29H21NO5.0.40 C4H8O.0.22 H2O Calc'd: C, 74.06; H, 5.00; N, 2.82. Found: C, 73.83; H, 5.19; N, 2.70.

Provenance & Evidence