Methyl 5-aminopyridine-3-carboxylate synthesis
- Product Name:Methyl 5-aminopyridine-3-carboxylate
- CAS Number:36052-25-2
- Molecular formula:C7H8N2O2
- Molecular Weight:152.15
67-56-1
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24242-19-1
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36052-25-2
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Yield: 86%
Reaction Conditions:
with thionyl chloride at 0;Reflux;
Steps:
IV-16.1
To a stirred solution of 5-amino-nicotinic acid (10.0 g, 72.5 mmol) in methanol (100 mL) was added SOCl2 (10.4 g, 86.9 mmol) dropwise at 0°C. The mixture was allowed warm to room temperature and then refluxed for 16 hours. The mixture was cooled, concentrated in vacuum and the residue was diluted with water (200 mL). The mixture was neutralized with aqueous NaHC03 solution to pH = 7. The aqueous mixture was extracted with DCM (100 mL x2). The combined organic layers were washed with brine (100 mL x2), dried over anhydrous Na2S04, filtered and the filtrate was concentrated in vacuum to dryness to give 9.5 g (yield: 86%) of 5-amino-nicotinic acid methyl ester as white solid. 1H NMR (DMSO-d6, 400MHz): δ = 8.24 (1H, d), 8.12 (1H, d), 7.42 (1H, dd), 5.65 (2H, brs), 3.84 (3H, s).
References:
SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE;PINKERTON, Anthony, B.;DAHL, Russell;COSFORD, Nicholas, D.P.;MILLAN, Jose, Luis WO2013/126608, 2013, A1 Location in patent:Paragraph 00492-00493
24242-19-1
266 suppliers
$6.00/1g
36052-25-2
138 suppliers
$7.00/250mg
24242-19-1
266 suppliers
$6.00/1g
18107-18-1
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$33.00/5g
36052-25-2
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$7.00/250mg
29681-44-5
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36052-25-2
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$7.00/250mg
20826-04-4
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$5.00/1g
36052-25-2
138 suppliers
$7.00/250mg