2-Amino-6-methyl-3-pyridinol

3-Hydroxy-6-methyl-2-nitropyridine (30 g, 194.6 mmol) was hydrogenated in ethanol solution at 50° C. using H2 at 5 psi and 20percent Pd(OH)2/C catalyst for 1 hour. Upon completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to get the desired product 1 as a brown solid (23.68 g, 98percent). NMR data was consistent with the proposed structure.2-amino-6-methylpyridin-3-ol; A mixture of 3-hydroxy-6-methyl-2-nitropyridine (20 g, 0.129 mol) and 10percent Pd/C (4 g) was stirred vigorously in a flow of hydrogen for 20 h. The catalyst was filtered off, washed with methanol, and the filtrate was evaporated to dryness to provide 15.5 g (97percent) of a brown crystalline solid. To a solution of 6-methyl-2-nitropyridin-3-ol (25.0 g, 162 mmol) in acetic acid (400 mL) was added 10percent palladium on carbon (50percent wet, 2.50 g) . The reaction mixture was purged with hydrogen and stirred under balloon pressure hydrogen for 13 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound (19.1 g, 153 mmol, 95percent) as a colorless powder. First Step A mixture of 3-hydroxy-6-methyl-2-nitropyridine (4.2 g, 27 mmol) and 10percent palladium on carbon (0.25 g, 0.24 mmol) in ethanol (75 mL) was stirred at rt under an atmosphere of hydrogen for 24 hr. The catalyst was removed by filtration through celite and the filtrate concentrated to dryness under vacuum. The residue was subjected to chromatography on silica gel using Biotage SP1 employing a 40+M cartridge and eluting with MeOH/DCM 10percent 2 CV, 10-35percent in 10 CV, 35percent 2 CV. The purified product 2-amino-6-methyl-3- pyridinol (D145, 2.72 g, 80percent) was isolated as pale brown solid.[M+H]

Molecular Weight:124.14
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:124.063662883
Monoisotopic Mass:124.063662883
Topological Polar Surface Area:59.1
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes