Methanol → 1,4-Pentanediamine, N(sup 4)-(6-methoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)-8-quinolinyl)-, butanedioate (1:1)

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Reaction Steps

A solution of the phthalimide VIII (4.9 g, 8.7 mmol) in ethanol (110 mL) containing hydrazine hydrate (75%, 1.48 mL) was heated at reflux for 6 hours. The ethanol was removed under reduced pressure and the residue was shaken with ether and 10% aqueous potassium hydroxide. The ether layer was washed with water (×2) and dried (K2CO3). To the dried ether solution of 1 as the free base, was added a solution of succinic acid (1.03 g, 1 mol equiv) in ether (100 mL) containing methanol (4 mL) to solubilize the succinic acid. After standing overnight, the solid was filtered to yield 4.5 g (94%) of the target compound (1), mp 102°-103° (eff).

Provenance & Evidence