4-Amino-2-methylpyridine

Light yellow Cryst

[2-METHYL-4-NITROPYRIDINE-N-OXIDE] (5 g, 32.4 mmol) and iron powder [(18. 1 G, ] 324 mmol) in [ACOH] (300 mL) was mechanically stirred at [70° C FOR] 3h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The pH of the residue was adjusted to pH [GT;] 10, by addition ofNaOH and a minimal amount-of water. The reaction mixture was taken up in a liquid-liquid extractor and extracted with CHC13 for 12 hours. The layers were separated, dried [(NA2S04)] and concentrated under vacuum to afford desired 4-amino-2-methylpyridine (3.5 g, >99percent yield).(3) A solution OF 2-METHYL-4-NITROPYRIDINE-N-OXIDE (3.80 g, 24.6 mmol) in 100 ML of acetic acid was slowly heated with iron powder (6.89 g, 124 mmol) in a large flask (caution: the reaction becomes very exothermic upon turning brown). The resulting slurry was heated for 2 hours at 80 C. Excess acetic acid was removed IN VACUO, THE residue was taken up in 20percent aqueous sodium hydroxide solution, and 100 mL of chloroform (CHC13) was added and the mixture filtered through CELITES FILTER aid. The aqueous phase was extracted with two 200 mL portions of chloroform. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product (2.2 g, 83percent yield) was used without further purification. A solution OF KI (1. 96 g, 11. 9 mmol) and 12 (1.87 g, 7.36 mmol) in 10 ML of water was added to a REFLUXING solution of the 2-methylpyridin-4-ylamine (1.00 g, 9.25 mmol) and sodium carbonate (683 mg, 6.44 mmol) in 5 ML of water. The mixture was heated at reflux for 2 hours, cooled to room temperature, and treated with 20 mL of ethyl acetate (EtOAc). Phases were separated and the aqueous layer was extracted with three 20 ML portions of ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium thiosulfate (NA2S203) solution, dried over magnesium sulfate, and concentrated ILL vacuo. Flash chromatography (30percent ethyl acetate in hexanes to 100percent ethyl acetate, gradient) of the resulting residue yielded 4-amino-3-iodo-6-methylpyridine (first eluting: 226 mg, 11percent yield) and 4- AMINO-3-IODO-2-METHYLPYRIDINE (second eluting : 116 mg; 5percent yield).4-Amino-2-methylpyridine (152)A stirred solution of 4-nitro-2-methylpyridine-iV-oxide (20 g, 0.13 mol) in AcOH (300 mL) is treated with iron powder (40 g, 0.72 mol) in one portion at RT. This grey suspension is then gently heated to 100°C and stirred 2 h. The reaction mixture is then filtered through celite, and the solids collected washed with acetonitrile (1 L). The dark brown filtrate is then reduced in vacuo, diluted with 6 M NaOH (500 mL) and extracted into TBME (4 x 200 mL). The TBME phases are combined, dried (MgSOSynthesis of Compound 3554-Amino-2-methylpyridine (152)A stirred solution of 4-nitro-2-methylpyridine-λ'-oxide (20 g, 0.13 mol) in AcOH (300 mL) was treated with iron powder (40 g, 0.72 mol) in one portion at RT. This grey suspension was then gently heated to 10O4-Amino-2-methylpyridine (152); A stirred solution of 4-nitro-2-methylpyridine-N-oxide (20 g, 0.13 mol) in AcOH (300 mL) is treated with iron powder (40 g, 0.72 mol) in one portion at RT. This grey suspension is then gently heated to 100°C and stirred 2 h. The reaction mixture is then filtered through celite, and the solids collected washed with acetonitrile (1 L). The dark brown filtrate is then reduced in vacuo, diluted with 6 M NaOH (500 mL) and extracted into TBME (4 x 200 mL). The TBME phases are combined, dried (MgSOSynthesis of Compound 355; 4-Amino-2-methylpyridine (152); A stirred solution of 4-nitro-2-methylpyridine-N-oxide (20 g, 0.13 mol) in AcOH(300 mL) is treated with iron powder (40 g, 0.72 mol) in one portion at RT. This grey suspension is then gently heated to 100

Molecular Weight:108.14
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:108.068748264
Monoisotopic Mass:108.068748264
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:72.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes