5-Ethoxy-6-methyl-2-pyridinamine

c) The nitropyridine above (176 g), IMS (1.6 l), reduced iron powder (179 g) and water (350 ml) were boiled under reflux. Heating was discontinued while concentrated hydrochloric acid (67 ml) was carefully added dropwise over 20 minutes. The mixture was boiled under reflux for 1.75 hours then cooled and filtered through a filtration aid. The filtrate was evaporated under reduced pressure. Water was added to the residue and the mixture basified with 5M sodium hydroxide. Extractive work-up (dichloromethane) gave 5-ethoxy-6-methylpyridin-2-amine, m.p. 93-96 C.c) The nitropyridine above (176 g), IMS (1.6 l), reduced iron powder (179 g) and water (350 ml) were boiled under reflux. Heating was discontinued while concentrated hydrochloric acid (67 ml) was carefully added dropwise over 20 minutes. The mixture was boiled under reflux for 1.75 hours then cooled and filtered through a filtration aid. The filtrate was evaporated under reduced pressure. Water was added to the residue and the mixture basified with 5M sodium hydroxide. Extractive work-up (dichloromethane) gave 5-ethoxy-6-methylpyridin-2-amine, m.p. 93-96 C.18.2 g of the nitro compound obtained above was suspended in 300 ml of ethanol, which was reduced over 2 g of 5% palladium black under atmospheric pressure. After reaction, the catalyst was filtered off and the solvent was evaporated in vacuo. The residue was crystallized from benzene to obtain 13.8 g of 3-ethoxy-2-methyl-6-aminopyridine (Compound IV where R2 =C2 H5), m.p. 98-99 C.b) The product from part a) (19.0 g) was added dropwise to 5M sodium hydroxide solution (29 ml) and water (100 ml) keeping the temperature below 15 C. This solution was then added quickly to the solution of 5-ethoxy-6-methyl-pyridin-2-amine (20.0 g) in 4M hydrochloric acid (40 ml) and water (200 ml). This mixture was stirred at ambient temperature for 2 hours then filtered to give a solid which was recrystallized from IMS/water to give ethyl 2-(5-ethoxy-6-methylpyridin-2-ylaminomethylene)propionate, m.p. 118-122 C.b) Ethyl 2-(ethoxymethylene)-3-oxohexanoate (22.4 g) was added to a suspension of

Molecular Weight:152.19
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:152.094963011
Monoisotopic Mass:152.094963011
Topological Polar Surface Area:48.1
Heavy Atom Count:11
Complexity:119
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes