Hydrazine → (6-Benzyl-2-pyridyl)methanol

HRID 27712

Reaction equation

HRID 27712 reaction equation
[C:1]([C:9]1[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].NN>C(O)COCCOCCO>[CH2:1]([C:9]1[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 20293448(6-Benzoyl-2-pyridyl)methanol

Product 1

HCID 20293444(6-Benzyl-2-pyridyl)methanol

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Procedure

A mixture of (6-benzoyl-2-pyridyl)methanol (1.5 g, 7 mmol), potassium hydroxide (1.3 g, 23 mmol) and hydrazine 85% (1 ml, 25 mmol) in triethylene glycol (10 ml) is refluxed for 1.5 hours, and then the water and excess hydrazine are removed by a takeoff condenser until the temperature rises to 195°-200°. After 4 hours at 195°-200°, the solution is cooled, poured into ice and water (50 ml) and extracted with ether (3×20 ml). The combined ether layers are washed with water (3×20 ml), brine (10 ml) and dried over calcium sulfate. Removal of solvents gives (6-benzyl-2-pyridyl)methanol.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. customthe water and excess hydrazine are removed by a takeoff condenser until the temperature
  3. customrises to 195°-200°
  4. temperaturethe solution is cooled
  5. additionpoured into ice and water (50 ml)
  6. extractionextracted with ether (3×20 ml)
  7. washThe combined ether layers are washed with water (3×20 ml), brine (10 ml)
  8. dry with materialdried over calcium sulfate
  9. customRemoval of solvents

Sources & evidence

ORD record
ord-01b3e29463704639923c10985c7aa2c5
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Linked notes

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