2,6-Dimethyl-4-pyridinamine

White to off-white solid

A solution OF 4-NITRO-2, 6-DIMETHYLPYRIDINE-N-OXIDE (11.0 g, 65.4 mmol) in 50 mL of acetic acid was treated with iron powder (21.8 g, 390 mmol) in small portions while the mixture was rapidly stirred and gradually heated to 50 C (caution: the reaction becomes very exothermic at this temperature). After the exotherm ceased, the mixture was heated for an additional hour at 80 C. The resulting solidified mixture was treated with 50 ML of water and the suspension was filtered through CELITE filter aid. The filtrate was treated with ca. 200 ML of 6 N sodium hydroxide solution until the pH of the solution was basic (>12). The resulting green suspension was extracted with three 300 mL portions of chloroform. The extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give yellowish crystals (5.70 g, 71percent yield). A solution of 2, 6-dimethylpyridin-4-ylamine (2.00 g, 16. 4 MMOL) in 5 mL of acetic acid was treated dropwise with a solution of bromine (0.84 mL, 16.3 mmol) in 2 N-LL of acetic acid at room temperature in a water bath over a period of 10 minutes. After 1 hour, the resulting slurry was treated with 40 mL of 20percent sodium hydroxide solution and extracted with three 100 ML portions of dichloromethane (CH2CL2). The combined extracts were dried over magnesium sulfate, filtered, and concentrated IT7 VACUO. The resulting solid (starting material-desired PRODUCT-DIBROMO BYPRODUCT (1: 3: 1) ) was dissolved in 100 ML OF HOT HEXANES AND HOT FILTERED TO remove the insoluble starting material. The filtrate was allowed to cool to room temperature, which gave the title product as fine white needles (1. 30 g, 40percent yield).A 2L autoclave was charged with 60.0 g of 2, 6-dimethyl-4-nitropyridine nitrogen oxide, 12.0 g of 10percent Pd/C catalyst, 1200 g of glacial acetic acid as a solvent, and hydrogenation at 100°C for 10 hours. The reaction pressure was: At 3 to 4 Pa, after completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove acetic acid and water, and the product was recrystallized from acetone to obtain 35 g of an off-white powder.

Molecular Weight:122.17
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:122.084398327
Monoisotopic Mass:122.084398327
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:82.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes