5-cyano-6-isopropoxynicotinic acid synthesis

7synthesis methods

Product Name:5-cyano-6-isopropoxynicotinic acid
CAS Number:1167416-76-3
Molecular formula:C10H10N2O3
Molecular Weight:206.2

1312008-56-2
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1167416-76-3
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Yield:-

Reaction Conditions:

Stage #1: methyl 5-cyano-6-[(1-methylethyl)oxy]-3-pyridinecarboxylatewith water;sodium hydroxide in isopropyl alcohol at 20; for 1.66667 h;Inert atmosphere;
Stage #2: with acetic acid in water; pH=3;

Steps:

2; 17

To a suspension of methyl 5-cyano-6-[(1-methylethyl)oxy]-3-pyridinecarboxylate (1.010 g, 4.59 mmol) (Description 16) in isopropanol (22 mL) was added 2M aqueous sodium hydroxide (2.87 ml, 5.73 mmol) and the reaction mixture stirred at RT, under nitrogen, for 1 h 40 min. The solvent was then removed in vacuo and the residue dissolved in water (30 mL), acidified with acetic acid to pH 3 and the mixture extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with water (50 mL), dried over a phase separator and the solvent removed in vacuo to afford a solid which was dried under high vacuum to afford the title compound as a white solid (9 1 mg). LCMS (A) m/z: 206 [ +1]⁺, Rt 1.04 min (acidic).

References:

WO2011/72488,2011,A1 Location in patent:Page/Page column 16; 33