4-Methylnicotinic acid

White powder

Compound 3 (1.2 kg, 10.2 mol) was added to the mixtureof sodium hydroxide (1.6 kg, 40.6 mol) and 70percent ethanolaqueous solution (7.2 L). The solution was stirred under refluxfor 2 h. After being cooled to room temperature, concentratedhydrochloric acid (4.06 L) was dropped to the mixture.Then the solvent was removed under reduced pressureto afford white solid. The ethanol (10 L) was added to theresidual and heated to reflux for 10 min. After filtration, theethanol was evaporated under reduced pressure (20 mmHg)to afford compound 1 as white solid (1.33 kg, 96percent).Mp 215-216oC (lit. 215-217oC) [21]. IR (KBr): 2423 cm-1(O-H), 1721 cm-1 (C=O). 1H NMR (DMSO-d6, 300 MHz):11.9 (br s, 1H), 9.00 (s, 1H), 8.72 (d, J = 4.9 Hz, 1H), 7.67(d, J = 4.9 Hz, 1H), 2.67 (s, 3H). 13C NMR (DMSO-d6, 75MHz): 179.7, 166.4, 153.9, 148.2, 147.6, 128.3, 21.4. MS(ESI): m/z 138.1 [M+H]+, 136.1 [M-H]-.4-Methyl-nicotinic acid4-Methyl-nicotinic acid4-Methyl-nicotinic acid methyl ester (15 g, 0.1 mol) was added into the mixture of aqueous NaOH (2 M, 55 mL) and dioxane (100 mL), then the reactant was heated to 50-60 °C for 1 hour. The solvent was removed in vacuo. The residue was diluted with water (20 mL) and acidified by IN HC1 to PH~6, the solid formed was filtered and dried in vacuo to give 8.0 g of 4-methyl-nicotinic acid as a white solid in 58.4 percent yield.4-Methyl-nicotinic acid methyl ester (15 g, 0.1 mol) was added into the mixture of aqueous NaOH (2 M, 55 mL) and dioxane (100 mL), then the reactant was heated to 50˜60° C. for 1 hour.

Molecular Weight:137.14
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:50.2
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes