Water → 4-Pentylbicyclo[2.2.2]octane-1-carbohydrazide

HRID 1784482Notes

Reaction equation

HRID 1784482 reaction equation
[NH2:1][NH2:2].[CH2:3]([C:8]12[CH2:15][CH2:14][C:11]([C:16]([O:18]C)=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)[CH2:4][CH2:5][CH2:6][CH3:7].O>C(O)CO>[CH2:3]([C:8]12[CH2:15][CH2:14][C:11]([C:16]([NH:1][NH2:2])=[O:18])([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 22591715Methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 225916944-Pentylbicyclo[2.2.2]octane-1-carbohydrazide

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

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 N (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.

Workup

  1. temperatureunder reflux for 17 h
  2. extractionextracted with methylene chloride (3×600 mL)
  3. washThe combined extracts were washed twice with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6f2bd4daaeb4b90bd37aa6b589eab91
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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