Methyl-6-chloro-5-nitronicotinate Chemical Properties

Melting point:

76 °C

Boiling point:

317.8±37.0 °C(Predicted)

Density 

1.500±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

HS Code 

2933399990

Methyl-6-chloro-5-nitronicotinate Usage And Synthesis

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

Methyl-6-chloro-5-nitronicotinate 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

Methyl-6-chloro-5-nitronicotinate(59237-53-5)Related Product Information

• 2-Pyridinamine, 6-chloro-5-methyl
• METHYL 6-CHLORO-5-IODONICOTINATE
• 2-Pyridinecarboxylic acid, 6-chloro-5-hydroxy-
• 2-Chloro-3-nitro-5-pyridinecarboxylic acid
• 5-Aminonicotinic acid
• Methyl 6-chloronicotinate
• 5-AMINO-NICOTINIC ACID METHYL ESTER
• Methyl-6-chloro-5-nitronicotinate
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• 2-CHLORO-3-NITROPYRIDINE
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• 4,6-Dichloro-5-nitronicotinic acid ethyl ester
• 5-Amino-6-chloro-3-pyridinecarboxylic acid methyl ester
• 5-NITRONICOTINALDEHYDE
• LABOTEST-BB LT01148420