2-Methoxy-4-pyridinecarboxylic acid synthesis
- Product Name:2-Methoxy-4-pyridinecarboxylic acid
- CAS Number:105596-63-2
- Molecular formula:C7H7NO3
- Molecular Weight:153.14
15855-06-8
105596-63-2
General procedure for the synthesis of 2-methoxy-4-pyridinecarboxylic acid from 2-chloro-6-methoxyisonicotinic acid: To a suspension of acetonitrile (150 mL) containing 2-methoxy-4-pyridinecarboxylic acid (1.94 g, 6.49 mmol) was added sodium iodide (4.90 g, 32.69 mmol) and trimethylmethylsilyl chloride (4.10 mL, 32.42 mmol). The reaction mixture was stirred at 40 °C for 3 days under nitrogen protection. After completion of the reaction, the mixture was cooled to 0 °C, the solid product was collected by filtration, washed with acetonitrile and dried to afford 1.66 g (90% yield) of the target compound, 2-methoxy-4-pyridinecarboxylic acid.LRMS: m/z 285 (M + 1)+; retention time: 2.86 min (Method B).
15855-06-8
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105596-63-2
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Yield:105596-63-2 78%
Reaction Conditions:
with hydrogen;triethylamine;palladium 10% on activated carbon in methanol at 20; under 155.149 Torr;
Steps:
64
To a suspension of the title compound of Preparation 22 (1.94 g, 6.49 mmol) in acetonitrile (150 mL), sodium iodide (4.90 g, 32.69 mmol) and trimethylsilyl chloride (4.10 mL, 32.42 mmol) were added. The resulting suspension was stirred under nitrogen atmosphere at 400C for 3 days. The mixture was cooled to O0C and the solid was filtered off, washed with acetonitrile and dried to yield 1.66 g (90%) of the title compound.LRMS: m/z 285(M+1 )+ Retention time: 2.86min (method B)
References:
ALMIRALL, S.A.;GRIMA POVEDA, Pedro Manuel;AGUILAR IZQUIERDO, Nuria;MIR CEPEDA, Marta;LOPEZ MARTINEZ, Manuel WO2010/43377, 2010, A1 Location in patent:Page/Page column 64
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