Methyl-6-chloro-5-nitronicotinate synthesis
- Product Name:Methyl-6-chloro-5-nitronicotinate
- CAS Number:59237-53-5
- Molecular formula:C7H5ClN2O4
- Molecular Weight:216.58
67-56-1
776 suppliers
$7.29/5ml-f
6635-31-0
226 suppliers
$8.00/1g
59237-53-5
175 suppliers
$11.00/250mg
Yield:59237-53-5 90%
Reaction Conditions:
Stage #1:6-hydroxy-5-nitronicotinic acid with thionyl chloride;N,N-dimethyl-formamide for 8 h;Reflux;
Stage #2:methanol in dichloromethane at -40 - -30;
Stage #3: with sodium hydrogencarbonate in dichloromethane;water at -30 - 20;
Steps:
1
DMF (0.15 eq) was added to a solution of β-hydroxy-S-nitronicotinic acid (1 eq) in SOCl2 (4.7 eq). The mixture was heated at reflux for 8 h then concentrated in vacuo. The residue was taken up in CH2Cl2, cooled to -400C, and MeOH (1.4 eq) added while maintaining the internal temperature below -300C. Aqueous NaHCO3 (1 eq) was added and the mixture allowed to warm to room temperature. The organic phase was separated and concentrated in vacuo. The crude residue was crystallized from EtOH to give methyl 6-chloro-5-nitronicotinate (90 % yield)
References:
SIRTRIS PHARMACEUTICALS, INC.;OALMANN, Christopher;DISCH, Jeremy, S.;NG, Pui, Yee;PERNI, Robert, B. WO2010/71853, 2010, A1 Location in patent:Page/Page column 68
7477-10-3
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$6.00/250mg
74-88-4
351 suppliers
$15.00/10g
59237-53-5
175 suppliers
$11.00/250mg
67-56-1
776 suppliers
$7.29/5ml-f
59237-53-5
175 suppliers
$11.00/250mg
7477-10-3
118 suppliers
$6.00/250mg
18107-18-1
214 suppliers
$33.00/5g
59237-53-5
175 suppliers
$11.00/250mg
67-56-1
776 suppliers
$7.29/5ml-f
7477-10-3
118 suppliers
$6.00/250mg
59237-53-5
175 suppliers
$11.00/250mg