5-cyano-3-methylpyridine-2-carboxylic acid synthesis
- Product Name:5-cyano-3-methylpyridine-2-carboxylic acid
- CAS Number:1262860-49-0
- Molecular formula:C8H6N2O2
- Molecular Weight:162.15
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Yield:1262860-49-0 94%
Reaction Conditions:
with trifluoroacetic acid in dichloromethane at 20; for 2 h;
Steps:
37.3 Synthesis of 5-cyano-3-methylpicolinic acid
To a solution of tert-butyl 5-cyano-3-methylpicolinate (4.18 g, 19.15 mmol) in DCM (96 ml) was added TFA (148 ml, 1915 mmol), and the brown solution was stirred at RT for 2 h. The reaction mixture was concentrated. To the brown red residue was added EtOAc and it changed into a yellow slurry. It was concentrated again and dried on high vacuum. The reaction was triturated with 30 mL of MTBE and 50 ml of hexanes to yield 5-cyano-3-methylpicolinic acid (2.91 g, 17.95 mmol, 94% yield) as yellow solid. MS m/z=163.2 (M+H).
References:
US2014/213581,2014,A1 Location in patent:Paragraph 0757; 0760
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