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ChemicalBook CAS DataBase List 2,6-DIMETHYLISONICOTINIC ACID
54221-93-1

2,6-DIMETHYLISONICOTINIC ACID synthesis

8synthesis methods
Synthesis of 2,6-dimethylisonicotinic acid: A mixture of 4-cyano-2,6-dimethylpyridine (0.5 g, 3.78 mmol), sodium hydroxide (2.5 M, 3 ml) and ethanol (3 ml) was reacted at 100 °C for 5 hours. After cooling to room temperature, the solution was concentrated under vacuum and acidified to pH 3 with 10% hydrochloric acid. After evaporation to dryness, 2,6-dimethylisonicotinic acid was obtained[1].
-

Yield:-

Reaction Conditions:

with sulfuric acid at 100; for 5 h;

Steps:

1.a 2,6-Dimethylisonicotinic Acid (2)

A mixture of 1 g (7.56 mmol) of (1) and 5 ml of concentrated sulfuric acid is heated at 100° C. for 5 hours. The resulting solution is then cooled on an ice bath, brought to pH 3.5 with 10 N sodium hydroxide and then concentrated to dryness. Extraction with ether for 48 hours (soxhlet) of a portion of the residue obtained gives 50 mg of 2,6-dimethylisonicotinic acid (2) for analysis. The remaining crude reaction product, not treated with ether, is used in its present form in the esterification reaction without further purification. [0133] NMR: 1H (D20); internal reference tBuOH 1.29 ppm. [0134] 2.82 (s, 6H, CH3); 8.05 (s, 2H, Py). [0135] MS (EI): 151 (M+, 100); 134 (M+-OH, 7.2); 106 (M+-CO2H, 16.4) [0136] MA: C8H9NO2+0.1 NaHSO4 (163.16) [0137] calculated: C 58.89H 5.62 N 8.58 O 23.53 [0138] found: C 58.73H 5.90 N 8.37 O 23.7

References:

US2004/92726,2004,A1 Location in patent:Page 7

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