| Identification | Back Directory | [Name]
methyl 3-bromo-4-methyl-5-nitropicolinate | [CAS]
1150618-07-7 | [Synonyms]
methyl 3-bromo-4-methyl-5-nitropicolinate
methyl3-bromo-4-methyl-5-nitropyridine-2-carboxylate
methyl 3-bromo-4-methyl-5-nitropicolinate ISO 9001：2015 REACH
3-Bromo-4-methyl-5-nitro-2-pyridinecarboxylic acid methyl ester
2-Pyridinecarboxylic acid, 3-bromo-4-methyl-5-nitro-, methyl ester | [EINECS(EC#)]
200-589-5 | [Molecular Formula]
C8H7BrN2O4 | [MDL Number]
MFCD12031253 | [MOL File]
1150618-07-7.mol | [Molecular Weight]
275.06 |
| Hazard Information | Back Directory | [Preparation]
Methyl-3-bromo-4-methyl-5-nitropicolinate synthesis: 3-bromo-2-iodo-4-methyl-5-nitropyridine (129.0 g, 0.38 mol) and (Ph3P)2PdCl2 (7.92 g, 3 mol%) were suspended in CH3CN (1300 mL) and MeOH (430 mL) and Et3N (79.3 mL, 1.5 eq) was added. The mixture was transferred to a steel 5000 mL pressure vessel, 4 bar of CO pressure was applied and the reaction mixture was slowly heated to 80 oC. Subsequently, it was stirred for 5 h at this temperature, then allowed to cool overnight. The volatiles were removed in vacuo, the residue was stirred in EtOAc (1000 mL) and filtered. The residue was extracted with EtOAc (2*250 mL) and the combined filtrates were washed with brine (1000 mL) and dried on Na2SO4. The volatiles were removed in vacuo, affording 120 g of a brown oil. This was coated on 120 g of silicagel and purified by column chromatography (3500 g of silica gel, EtOAc/heptane 1:3, KMnO4 staining). The appropriate fractions were combined and concentrated to give Methyl-3-bromo-4-methyl-5-nitropicolinate as a beige solid (63.5 g, 61%). |
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