2,3-Dichloroquinoxaline → 2-Chloro-3-hydrazinoquinoxaline

HRID 464279

Reaction equation

HRID 464279 reaction equation
[Cl:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.[NH2:14][NH2:15]>C(O)C>[Cl:1][C:2]1[C:11]([NH:14][NH2:15])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 166592,3-DichloroquinoxalineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 36588202-Chloro-3-hydrazinoquinoxalineYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-Dichloroquinoxaline (33.5 g., 0.168 mole) was stirred with hydrazine hydrate (18.5 g., 0.369 mole) in 500 ml. of ethanol at room temperature overnight (i.e.. at ca. 20° C. for approximately 16 hours). The thick, yellow slurry was filtered and the precipitate was washed with ethanol. The precipitated material was recrystallized from hot methanol to give 13.5 g. (41% yield) of 2-chloro-3-hydrazinoquinoxaline, m.p. 181° C. (decomp.). Mass spectrum: m/e, 194 (P).

Workup

  1. customat room temperature
  2. customovernight (i.e.. at ca. 20° C. for approximately 16 hours)
  3. filtrationThe thick, yellow slurry was filtered
  4. washthe precipitate was washed with ethanol
  5. customThe precipitated material was recrystallized from hot methanol
  6. customto give 13.5 g

Sources & evidence

ORD record
ord-a221652dd3ff4eb0a45c35470f69b1ee
Source dataset
uspto-grants-1985_10
Patent number
US04547501

Linked notes

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