2-Chloroquinoline → Quinoline, 2-hydrazinyl-

HRID 962753Notes

Reaction equation

HRID 962753 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.[NH2:13][NH2:14]>C(O)C.O>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[NH:13][NH2:14]

Participants

5

Reactant 2

HCID 119282-ChloroquinolineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 85111Quinoline, 2-hydrazinyl-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloroquinoline (15 g) in ethanol (150 ml) was added hydrazine hydrate (40 ml) the resulting solution was heated at reflux for 6 hrs then diluted with water (400 ml) and extracted with diethyl ether (3×200 ml). The collected organic phase was washed with brine (300 ml), dried and concentrated under vacuum to afforg the title compound as a solid (13 g)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. extractionextracted with diethyl ether (3×200 ml)
  4. washThe collected organic phase was washed with brine (300 ml)
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bf4824fec83f4f6487b276a291e8fc17
Source dataset
uspto-grants-1998_06
Patent number
US05760059

Reaction notes

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