2-Amino-3-pyridineacetic acid

The residue 6 was dissolved in 6 N HCl and refluxed overnight. Adjustment with 6 N NaOH to pH 5 produced a precipitate, that was collected by filtration to afford 7 as a white solid (2 g, 12.0 mmol, 38percent). The mother liquor of the foregoing example was extracted three times with an equal volume of ethyl acetate and the combined organic phases were dried over sodium sulphate. Removal of the solvent afforded the product as colourless solid. A suspension of In a 100 mL 2-neck round bottom flask, and under a nitrogen atmosphere, was added The residue 6 was dissolved in 6 N HCl and refluxed overnight. Adjustment with 6 N NaOH to pH 5 produced a precipitate, that was collected by filtration to afford 7 as a white solid (2 g, 12.0 mmol, 38%). 1H NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 7.83 (dd, 1H, 3JH, H = 4.8 Hz, 4JH, H = 1.4 Hz), 7.26 (dd, 1H, 3JH, H = 7.2 Hz, 4JH, H = 1.4 Hz, ), 6.50 (dd, 1H, 3JH, H = 7.2 Hz, 4JH, H = 5.1 Hz), 5.70, (s, 3H) 3.42 (s, 2H).PREPARATIVE STR51 To a stirred solution of 96 g (0.5 mole) of 2-(trimethylacetylamino)-3-methylpyridine in 1500 mL of dry tetrahydrofuran at -10 C. is added 423 mL of 2.6M n-butyllithium-hexane solution dropwise over one hour. The mixture is maintained at -5 to 0 C. for 4 hours and then poured into a stirred suspension of 1.5 kg of dry ice powder in 700 mL of diethyl ether. Solvent is removed at reduced pressure and the resulting solid residue mixed with 1200 mL of 3N hydrochloric acid, and refluxed for 4 hours. 1000 mL of water are removed at reduced pressure and the remaining solution is neutralized with 10% NH4 OH. The precipitated 50 mL of n-butyllithium in hexane (1.6 M, 80 mmol) were slowly added to a solution of 2-(trimethylacetylamino)-3-methylpyridine (6.15 g, 32 mmol) in dry THF (90 mL) at -78 C in a period of 1 h. The mixture was stirred at -78 C for 1 h and at -20 C for 3 h. Powdered dry ice was added to this suspension at -78 C. The mixture was allowed to warm up to room temperature, diluted with water and acidified with 4 N HCl to pH = 5. The mixture was extracted three times with an equal volume of ethyl acetate and the organic layer was dried over magnesium sulphate. After removal of the solvent the residue was dissolved in 6 N HCl and refluxed overnight. Neutralization with 6 N NaOH (pH = 5) produced a precipitate, that was collected by filtration to afford a colourless solid (2 g, 12.0 mmol, 38 %). 1H-NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 7.83 (dd, 1H, 3JH, H= 4.8 Hz, 4JH, H = 1.4 Hz, 6-CH), 7.26 (dd, 1H, 3JH, H = 7.2 Hz, 4JH, H = 1.4 Hz, 4-CH), 6.50 (dd, 1H, 3JH, H = 7.2 Hz, 4JH, H = 5.1 Hz, 5-CH), 5.70, (s, 3H, NH3+), 3.42 (s, 2H, CH2).

Molecular Weight:152.15
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:152.058577502
Monoisotopic Mass:152.058577502
Topological Polar Surface Area:76.2
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes