ChemicalBook CAS DataBase List Methyl-6-chloro-5-nitronicotinate

Methyl-6-chloro-5-nitronicotinate synthesis

7synthesis methods

Product Name:Methyl-6-chloro-5-nitronicotinate
CAS Number:59237-53-5
Molecular formula:C7H5ClN2O4
Molecular Weight:216.58

67-56-1 Synthesis

67-56-1
759 suppliers
$7.29/5ml-f

6635-31-0 Synthesis

6635-31-0
215 suppliers
$8.00/1g

59237-53-5
174 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

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7477-10-3 Synthesis