3-(METHOXYCARBONYL)ISONICOTINIC ACID synthesis

4synthesis methods

Product Name:3-(METHOXYCARBONYL)ISONICOTINIC ACID
CAS Number:24202-79-7
Molecular formula:C8H7NO4
Molecular Weight:181.15

3,4-Pyridinedicarboxylic acid dimethyl ester

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Yield:-

Reaction Conditions:

with water;sodium hydroxide at 0 - 20;

Steps:

Intermediate A8: Pyridine-3,4-dicarboxylic acid 3-methyl ester

To a suspension of pyridine-3,4-dicarboxylic acid dimethyl ester Intermediate A7(5.26 g, 27.0 mmol) in water (50 mL) was added a solution of sodium hydroxide (1.08 g27.0 mmol) in water (16 mL) at 0 °C. The mixture was stirred at room temperatureovernight during which time the mixture became homogeneous. Extraction with chloroform removed unconsumed diester and the remained aqueous layer was acidified to pH 1 with concentrated hydrochloric acid. The resulting solution was evaporated to dryness under reduced pressure at 30 °C. Extraction of the generated residue with hottetrahydrofuran gave the crude mono-ester, which was recrystallized from methanol (1.0 g crude mono-ester in 3 mL methanol from 80 °C to room temperature) to give the title compound (2.0 g, 34 % yield) as gray solids. LC-MS (ESI): RT = 0.25 mm, mass calcd. for C8H7N04 181.0, mlz found 182.3 [M+H]. ‘H NIVIR (300 1VIHz, DMSO-d6) 8.94 (s, 1H), 8.86 (d, J= 4.8 Hz, 1H), 7.68 (d, J 4.8 Hz, 1H), 3.85 (s, 3H).

References:

WO2019/1420,2019,A1 Location in patent:Page/Page column 40

490-11-9 Synthesis