4-Pyridinecarboxylic acid, 2-chloro-, methyl ester

White to light brown solid

To a solution of 2-chloroisonicotinic acid (2.0 g, 0.0 12 mole) in DMF (5 mL)under N2 at 25 °C, was added sodium hydride (0.73 g, 0.0 15 mole) and stirred for 0.5hour. Methyl iodide (1.5 mL, 0.025 mole) was added at RT and the reaction mixturewas warmed to 50 °C for 2 hours. The reaction mixture was dissolved in ice water (50mL) and extracted with ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL) and dried over Na2SO4. The organic phase was concentrated under vacuum to obtain methyl 2-chloroisonicotinate. Yield: 2.1 g (100 percent); Mass (mlz): 172.0 (M+H) , 174.0 (M+H) .Step 1: A mixture of 2-chloro-isonicotinic acid (4.0 g, 25.4 mmol), sodium bicarbonate (5.33 g, 63.48 mmol) and iodomethane (9.7 mL, 156.0 mmol) in N, N dimethyl formamide (60 mL) is stirred at room temperature for 20 hours. The mixture is poured into water and extracted with ether. The organic layer is washed with brine, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate provides an oil which solidifies on standing to yield 3.8 g (87percent) of 2-chloro-isonicotinic acid methyl ester as a white solid. MS 172.0 [M+H].2-Chloro-isonicotinic acid (5.10 g, 32.38 mmol) was dissolved in methanol (150 mL). Thionyl chloride (12 mL) was added. This suspension was stirred 5 h at 70 To a solution of 2-chloroisonicotinic acid 19-1 A (5 g, 31.8 mmol) in MeOH (50 mL) was added SOClPreparation 1; SYNTHESIS OF 2-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]ISONICOTINIC ACID METHYL ESTER; A. A mixture of 2-chloroisonicotinic acid (1.000 g, 6.340 mmol) and 5 drops of concentrated sulfuric acid in anhydrous methanol (50 mL) was refluxed for 3 hours. The reaction mixture was concentrated in vacuo, diluted with 20 mL of water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried and concentrated. The compound obtained was used for next step reaction without further purification. Yield 0.816 g, 75percent.Step 1 Step 2

Molecular Weight:171.58
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:171.0087061
Monoisotopic Mass:171.0087061
Topological Polar Surface Area:39.2
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes