Hydrazine hydrate (1:1) → 6-Chloro-2-hydrazinyl-4-phenylquinoline

HRID 1974052Notes

Reaction equation

HRID 1974052 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.O.[NH2:20][NH2:21]>>[Cl:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:20][NH2:21])[CH:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 43246192,6-dichloro-4-phenylquinoline

Product 1

HCID 126119386-Chloro-2-hydrazinyl-4-phenylquinolineYield 67%

Procedure

A stirred mixture of 2,6-dichloro-4-phenylquinoline (2.7 g., 0.01 mole) and hydrazine hydrate (6.8 g.) is refluxed under nitrogen for 1 hour and concentrated in vacuo. The residue is suspended in warm water, and the solid is collected by filtration, dried and recrystallized from ethyl acetate-Skellysolve B hexanes to give 1.81 g. (67% yield) of 6-chloro-2-hydrazino-4-phenylquinoline of melting point 156.5°- 157° C.

Workup

  1. temperatureis refluxed under nitrogen for 1 hour
  2. concentrationconcentrated in vacuo
  3. filtrationthe solid is collected by filtration
  4. customdried
  5. customrecrystallized from ethyl acetate-Skellysolve B hexanes
  6. customto give 1.81 g

Sources & evidence

ORD record
ord-caaa233562b94e8eb6b40eb72971ef33
Source dataset
uspto-grants-1976_12
Patent number
US04000151

Reaction notes

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