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

A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (500 mg), hydrazine monohydrate (147 mg), and ethanol (5 ml) was refluxed for 40 minutes 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 4-ethyl-2,4-hexadien-1-ylamine (205 mg) as an oil. This oil was used in the next reaction without further purification. To a solution of crude 4-ethyl-2,4-hexadien-1-ylamine (205 mg) in dichloromethane (2 ml) at 0° C. was added dropwise acetic anhydride (335 mg). After one hour, the reaction mixture was evaporated to dryness. The residue was chromatographed on silica gel (2% methanol in dichloromethane) to give 1-acetylamino-4-ethyl-2,4-hexadiene (122 mg) as an oil.

1. temperaturewas refluxed for 40 minutes 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-9350c494c9e44e9595cf9e4f19f85056

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691366