2-Chloroquinoline → Quinoline, 2-hydrazinyl-

HRID 1870956Notes

Reaction equation

HRID 1870956 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 hours 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), 1H--NRM (DMSO); 4.29(s,2H), 6.83 (d,1H), 7.15(m,1H), 7.47(m,1H), 7.52(d, 1H), 7.62(dd, 1H), 7.86(d,1H), 8.05(s,1H)

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 6 hours
  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-6b69057a1d104e5697f3c766e3a23b95
Source dataset
uspto-grants-2000_08
Patent number
US06100289

Reaction notes

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