| Identification | Back Directory | [Name]
Methyl-6-chloro-5-nitronicotinate | [CAS]
59237-53-5 | [Synonyms]
NSC 405361
Methyl-6-chloro-5-nitronicotite
Methyl-6-chloro-5-nitronicotinate
Methyl 6-chloro-5-nitro-3-pyridylate
methyl 6-chloro-5-nitronicotinic acid
6-Chloro-5-nitro-3-pyridinecarboxylic acid
6-chloro-5-nitropyridine-3-carboxylic acid
methyl 6-chloro-5-nitronicotinate(SALTDATA: FREE)
6-Chloro-5-nitropyridine-3-carboxylic acid methyl ester
6-Chloro-5-nitro-3-pyridinecarboxylic acid Methyl ester
3-Pyridinecarboxylic acid, 6-chloro-5-nitro-, Methyl ester
Methyl 6-chloro-5-nitropyridine-3-carboxylate, 2-Chloro-5-(methoxycarbonyl)-3-nitropyridine | [Molecular Formula]
C7H5ClN2O4 | [MDL Number]
MFCD01928341 | [MOL File]
59237-53-5.mol | [Molecular Weight]
216.58 |
| Chemical Properties | Back Directory | [Melting point ]
76 °C | [Boiling point ]
317.8±37.0 °C(Predicted) | [density ]
1.500±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
-4.81±0.10(Predicted) | [color ]
Off-white to grey | [InChI]
InChI=1S/C7H5ClN2O4/c1-14-7(11)4-2-5(10(12)13)6(8)9-3-4/h2-3H,1H3 | [InChIKey]
BRPREIDVQXJOJH-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=C([N+]([O-])=O)C=C1C(OC)=O |
| Hazard Information | Back Directory | [Description]
Methyl 6-chloro-5-nitronicotinate (CAS No. 59237-53-5), also known as methyl 6-chloro-5-nitropyridine-3-carboxylate , has the molecular formula C₇H₅ClN₂O₄ and a molecular weight of 216.58 . It is an important pharmaceutical intermediate, mainly used in the synthesis of a variety of drugs, including PARP inhibitors, immunomodulators and sulfonamide nicotinic acid derivatives (used to prepare drugs for the treatment of atherosclerosis). | [Uses]
6-Chloro-5-nitronicotinic Acid Methyl Ester, is a building block used for the synthesis of various pharmaceutical compounds, such as anticoccidial agents. | [Synthesis]
The general procedure for the synthesis of methyl 6-chloro-5-nitronicotinate from methanol and 5-nitro-6-hydroxynicotinic acid was as follows: DMF (0.15 eq.) was added to a solution of 5-nitro-6-hydroxynicotinic acid (1 eq.) in SOCl2 (4.7 eq.). The reaction mixture was heated to reflux for 8 hours followed by vacuum concentration. The concentrated residue was dissolved in CH2Cl2 and the solution was cooled to -40°C. Methanol (1.4 eq.) was slowly added while keeping the internal temperature below -30°C. Subsequently, an aqueous NaHCO3 solution (1 eq.) was added and the mixture was gradually warmed to room temperature. The organic phase was separated and concentrated under vacuum. Finally, the crude product was purified by crystallization from ethanol to afford methyl 6-chloro-5-nitronicotinate in 90% yield. | [References]
[1] Patent: WO2010/71853, 2010, A1. Location in patent: Page/Page column 68
[2] Patent: WO2016/183114, 2016, A1. Location in patent: Page/Page column 66
[3] Patent: EP2527344, 2012, A1. Location in patent: Page/Page column 24
[4] Patent: WO2012/160030, 2012, A1. Location in patent: Page/Page column 69
[5] Tetrahedron Letters, 2012, vol. 53, # 5, p. 535 - 538 |
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