Hydrazine → HCID 22132608, compound

HRID 1856757Notes

Reaction equation

HRID 1856757 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4=CC=CC=C4C3=O)[CH:8]=2)[N:3]=1.NN>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22132578HCID 22132578, compound

Product 1

HCID 22132608HCID 22132608, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-chloro-6-(3-phthalimidopropoxy)quinoline (9.0 g) in ethanol (250 ml) is added hydrazine.monohydrate (1.4 g), and the mixture is refluxed for 7.5 hours. The mixture is allowed to cool, and the precipitated crystals are collected by filtration, and suspended in water. The mixture is acidified with conc. hydrochloric acid, and stirred for one hour. The mixture is basified with a 10% aqueous potassium hydroxide solution, and extracted with chloroform. The extract is dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent to give 2-chloro-6-(3-aminopropoxy)quinoline (4.7 g) as a white powder.

Workup

  1. temperatureto cool
  2. filtrationthe precipitated crystals are collected by filtration
  3. extractionextracted with chloroform
  4. dry with materialThe extract is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-434043d0d2cf4f0da1684a5dbe1949fd
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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