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

HRID 22830Notes

Reaction equation

HRID 22830 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 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.

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-fa0bb4635fd947648b28211587d81055
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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