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17874-76-9

17874-76-9 Structure

17874-76-9 Structure
IdentificationBack Directory
[Name]

2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE
[CAS]

17874-76-9
[Synonyms]

6-(METHOXYCARBONYL)NICOTINIC ACID
6-Methoxycarbonylpyridine-3-carboxylicaci
(Methoxycarbonyl)pyridine-3-carboxylic acid
2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE
6-(Methoxycarbonyl)pyridine-3-carboxylic acid
2,5-Pyridinedicarboxylic acid, 2-methyl ester
5-Carboxy-2-(methoxycarbonyl)pyridine, 6-(Methoxycarbonyl)pyridine-3-carboxylic acid
[Molecular Formula]

C8H7NO4
[MDL Number]

MFCD09702182
[MOL File]

17874-76-9.mol
[Molecular Weight]

181.15
Chemical PropertiesBack Directory
[Melting point ]

161.5 °C(Solv: methanol (67-56-1))
[Boiling point ]

383.8±27.0 °C(Predicted)
[density ]

1.361±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

Solid
[pka]

3.04±0.10(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE(17874-76-9)MS
2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE(17874-76-9)1HNMR
2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE(17874-76-9)IR1
2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE(17874-76-9)IR2
Hazard InformationBack Directory
[Synthesis]

Methanol

67-56-1

2,5-PYRIDINEDICARBOXYLIC ACID

100-26-5

2-METHYL HYDROGEN PYRIDINE-2,5-DICARBOXYLATE

17874-76-9

The general procedure for the synthesis of 6-(methoxycarbonyl)nicotinic acid from methanol and 2,5-dipyridinecarboxylic acid is as follows: with reference to the literature method 66, a selective esterification reaction was first carried out on 2,5-pyridinedicarboxylic acid (58). 58 was dissolved in methanol, a catalytic amount of sulfuric acid was added and the reaction was refluxed for 2 hours. Upon completion of the reaction, the monomethyl ester product (59) was purified by recrystallization from water in 42% yield. Subsequently, the monomethyl ester 59 was converted to the corresponding acyl chloride (60) by reflux reaction with an excess of thionyl chloride. Finally, the acylation of compound 35 was completed using the reflux reaction of the chloride 60 with an excess of aluminum trichloride in dichloromethane (DCM) (Scheme 10).

[References]

[1] Patent: WO2011/103321, 2011, A1. Location in patent: Page/Page column 23
[2] Patent: US2006/293319, 2006, A1. Location in patent: Page/Page column 47
[3] Patent: WO2007/70173, 2007, A2. Location in patent: Page/Page column 145-146
[4] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928
[5] Patent: WO2012/121973, 2012, A1. Location in patent: Page/Page column 89
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