Phenylhydrazine → HCID 178469890, compound

HRID 2271098Notes

Reaction equation

HRID 2271098 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:11]([O:10][C:8]([C:7]1[C:2]2[C:3]([C:13](=[O:15])[N:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:25]=2)=[CH:4][NH:5][CH:6]=1)=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 18330002Diethyl 4-chloropyridine-3,5-dicarboxylate

Product 1

HCID 178469890HCID 178469890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 4-chloro-3,5-pyridinedicarboxylate (3.09 g, 12.0 mmol) and phenylhydrazine (1.42 ml, 14.4 mmol) in ethanol (100 ml) was degassed by evaporating under vacuum and refilling with nitrogen several times. The mixture was then stirred at reflux for 17 h under nitrogen. The mixture was left to cool in the fridge for a few hours, then filtered from a solid, which was washed with ethanol and ethyl acetate. The combined filtrates were evaporated in vacuo, and the residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) to afford 1.559 g (46%) as an orange solid; 1H NMR (360 MHz, DMSO-d6) δ1.35 (3H t, J 7.1 Hz), 4.34 (2H, q, J 7.1 Hz), 7.18 (1H, t, J 7.3 Hz), 7.44 (2H, t, J 7.5 Hz), 8.14 (1H, s), 8.19 (2H, d, J 7.6 Hz), 8.57 (1H, s), 12.49 (1H, br s).

Workup

  1. customwas degassed
  2. customby evaporating under vacuum
  3. temperatureat reflux for 17 h under nitrogen
  4. waitThe mixture was left
  5. temperatureto cool in the fridge for a few hours
  6. filtrationfiltered from a solid, which
  7. washwas washed with ethanol and ethyl acetate
  8. customThe combined filtrates were evaporated in vacuo
  9. customthe residue was purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2)
  10. customto afford 1.559 g (46%) as an orange solid

Sources & evidence

ORD record
ord-a5b6bda39af944ab9a064713debe0c99
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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