Ethanol → 4-Ethyl-2,4-hexadien-1-ylamine

A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (5.0 g), hydrazine monohydrate (2.45 g), and ethanol (150 ml) was refluxed for 1.5 hours under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give crude 4-ethyl-2,4-hexadien-1-ylamine (2.59 g) as an oil. The crude oil was dissolved in dichloromethane (30 ml) containing triethylamine (6.28 g). To this solution cooled to 0° C. was added nicotinic acid chloride hydrochloride (3.41 g) in small portions during 10 minutes. After 30 minutes, triethylamine (4.19 g) and nicotinic acid chloride hydrochloride (0.79 g) were added and the mixture was stirred for 30 minutes at 0° C. The reaction mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (2% methanol-dichloromethane) to give a mixture of N-[(2E,4E) and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-3-pyridinecarboxamide (4.6 g) which crystallized on standing.

1. temperaturewas refluxed for 1.5 hours under nitrogen atmosphere
2. temperatureAfter cooling
3. filtrationthe precipitate was filtered
4. washwashed with ethanol
5. customEvaporation of the filtrate
6. customgave a crystalline residue which
7. extractionextracted with dichloromethane
8. extractionThe organic extract
9. washwas washed with water and brine
10. dry with materialdried over anhydrous sodium sulfate
11. customevaporated

ORD record

ord-2b5ef39229af49ffb0ee8b81732e36f3

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05495023