“…The combined acid extracts were neutralized (Na2C03) and extracted with ether. The residue from the dried ethereal extracts was distilled, giving quinaldine (23.4 g), ethyl 2-quinolylacetate (18.6 g, 17%), bp 130-135°( 0.2 mm), and diethyl 2-quinolylmalonate (12) (25.6 g, 18%), bp 170-175°( 0.2 mm). The malonate 12 solidified on standing and was crystallized from petroleum ether as yellow needles: mp 72-73°( lit.7 mp 73-74°); ir 1630 cm"1; nmr (CCh) 1.28, 1.31 (overlapping t, 6, OCHCH), 4.24 (q, 4, OCHCH), 7-8.2 (m, 6, aromatic H); some specimens showed a sharp peak at 5.05, less than 1 H, due to tautomer; nmr (TFA) 1.45 (t, 6, OCHCH), 4.55 (q, 4, OCHCH), 5.75 [s, 1, CH-(C02Et)2], 8.0-8.6 (m, 5), and 9.28 (d, 1, / = 8 Hz, quinoline 4 H).…”