Hydrazine hydrate (1:1) → 2-(cyclohexylmethyl)-1H-pyrrole

A mixture of cyclohexyl pyrrol-2-yl ketone (17.7 g.) and 99% hydrazine hydrate (6.0 ml.) was heated under reflux in diethylene glycol (70 ml.) for 1.5 hours. The excess hydrazine hydrate and water were distilled off and the mixture was cooled. Potassium hydroxide (12.0 g.) was added portionwise and the mixture was then heated under reflux for 4 hours, cooled and poured into water (500 ml.). The mixture was extracted with ether (3×100 ml.) and the combined etheral extracts were washed with water (3×100 ml.) and dried over sodium sulphate. Evaporation of the ether gave an oil which was distilled to give 2-cyclohexylmethylpyrrole (11.3 g.), B.P. 137°-140° at 15 mm.

1. temperaturewas heated
2. distillationThe excess hydrazine hydrate and water were distilled off
3. temperaturethe mixture was cooled
4. additionPotassium hydroxide (12.0 g.) was added portionwise
5. temperaturethe mixture was then heated
6. temperatureunder reflux for 4 hours
7. temperaturecooled
8. additionpoured into water (500 ml.)
9. extractionThe mixture was extracted with ether (3×100 ml.)
10. washthe combined etheral extracts were washed with water (3×100 ml.)
11. dry with materialdried over sodium sulphate
12. customEvaporation of the ether
13. customgave an oil which
14. distillationwas distilled

ORD record

ord-3e4c6398f0aa4490a5084b040e8840c5

Source dataset

uspto-grants-1981_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04243672