4-{[3-cyano-4-(methoxymethyl)-6-methyl-2-pyridinyl]oxy}benzoic acid

4-{[3-cyano-4-(methoxymethyl)-6-methyl-2-pyridinyl]oxy}benzoic acid 3 was prepared by the reaction of the 2-chloro-3-cyanopyridine 1 with 4-hydroxybenzoic acid 2 using a literature procedure [1].

A mixture of 1.84g (10 mmol) of chlorocyanopyridine in 30 ml of ethanol, 1.38g (10 mmol) of

4-hydroxybenzoic acid and 1.12g (20 mmol) of potassium hydroxide in 8 ml water was boiled for 40 hours (water bath temperature). The reaction mixture was diluted with 5 ml of water and acidified with 10% aqueous hydrochloric acid until a precipitate formed. The precipitate was filtered and recrystallized from ethanol. Compound 3 - colourless solid. Yield 1.83g (61%).

M.p. 177°C (ethanol).

1H NMR (DMSO-d6, 60MHz): 2.38 (s, 3H, CH3); 2.53 (s, 3H, CH2OCH3); 4.64 (s, 2H, CH2OCH3); 7.23

(s, 1H, HHet), 7.32 (d, J=7Hz, 2H, HAr(1)), 8.03 (d, J=7Hz, 2H, HAr(2)), 11.72 (broad s, 1H, OH).

IR (vaseline oil, cm-1): 3270-3150, 3150-3050, 2230, 1725, 1630, 1625, 1575, 1520, 1480, 1415, 1400,

1360, 1240, 1195, 1145, 1050, 1020, 980, 920, 900, 870, 850, 815, 790, 725.

Anal. calc. for C16 H14 N2 O4 (298.29): C 64.42, H 4.73, N 9.39; found: C 64.31, H 4.45, N 9.42.