Reaction #51108

Reaction equation

Hydrazine

methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate

water

→

4-pentylbicyclo[2.2.2]octane-1-carbohydrazide

Solvents

ethylene glycol

Conditions

Workup

1. 1
   Temperatureunder reflux for 17 h
2. 2
   Extractionextracted with methylene chloride (3×600 mL)
3. 3
   WashThe combined extracts were washed twice with water, brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Concentrationconcentrated in vacuo

Procedure

Hydrazine (anhydrous, 103 mL, 88.7 mmol) was added to a solution of methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate (2-B) in ethylene glycol (180 mL) and the mixture was stirred under reflux for 17 h. After cooling to room temperature, the mixture was poured into water (1500 mL) and extracted with methylene chloride (3×600 mL). The combined extracts were washed twice with water, brine, dried (MgSO4) and concentrated in vacuo to provide 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide (2-C). 1H NMR (500 MHz, CDCl3): δ 0.90 (t, 3H); 1.21 (m, 8H); 1.43 (m, 6H); 1.74 (m, 6H); 3.85 (broad s, 2H); 6.81 (broad s, 1H) ppm.

Source