| Identification | Back Directory | [Name]
METHYL 5-METHYLNICOTINATE | [CAS]
29681-45-6 | [Synonyms]
METHYL 5-METHYLNICOTINATE
5-methylnicotin methyl ester
Methyl5-methylnicotinate,94%
5-Methyl-nicotinic acid methyl ester
Methyl 5-methylpyridine-3-carboxylate
3-Pyridinecarboxylicacid,5-methyl-,methylester(9CI)
Methyl 5-methylpyridine-3-carboxylate~5-Methylnicotinic acid methyl ester
Methyl 5-methylpyridine-3-carboxylate, 3-(Methoxycarbonyl)-5-methylpyridine | [EINECS(EC#)]
-0 | [Molecular Formula]
C8H9NO2 | [MDL Number]
MFCD01075739 | [MOL File]
29681-45-6.mol | [Molecular Weight]
151.16 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
46-48°C | [Boiling point ]
90°C 3mm | [density ]
1.104±0.06 g/cm3(Predicted) | [Fp ]
90°C/3mm | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in Chloroform and Methanol. | [form ]
Solid | [pka]
3.49±0.20(Predicted) | [color ]
White | [BRN ]
472498 | [InChI]
InChI=1S/C8H9NO2/c1-6-3-7(5-9-4-6)8(10)11-2/h3-5H,1-2H3 | [InChIKey]
KQILMMLAGGFMCM-UHFFFAOYSA-N | [SMILES]
C1=NC=C(C)C=C1C(OC)=O | [CAS DataBase Reference]
29681-45-6 |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
A metabolite of Nicotine. Used for the synthesis of (5-methylpyridin-3-yl)methanol, a key intermediate of Rupatadine fumarate. | [Synthesis]
S1, Preparation of methyl 5-methylnicotinate: Depending on the molar amount of 5-methylnicotinate, 16 equivalents of methanol were slowly added dropwise over a period of 20 minutes, followed by 3 equivalents of thionyl chloride. The reaction mixture was warmed up to 82°C and held at this temperature for 6 hours. Continuous stirring was required during the dropwise addition and during the holding phase. Upon completion of the reaction, the temperature was lowered to 55 °C and the excess methanol and thionyl chloride were removed by distillation under reduced pressure. The reaction mixture was cooled to room temperature and ice water was added to obtain solution A. The pH of solution A was adjusted with ammonia under ice bath conditions to 8. Subsequently, ethyl acetate was added for extraction. The separated ethyl acetate phase was dried by adding anhydrous sodium sulfate until the moisture content was reduced to 0.3% by weight. The dried solution was filtered and the ethyl acetate was removed by rotary evaporator to finally obtain methyl 5-methylnicotinate. | [References]
[1] Patent: EP2824103, 2015, A1. Location in patent: Paragraph 0039
[2] Patent: CN106560471, 2017, A. Location in patent: Paragraph 0054; 0060; 0066; 0072; 0078; 0084; 0090; 0096
[3] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205
[4] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[5] Biochemistry, 2010, vol. 49, # 49, p. 10421 - 10439 |
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