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

HRID 1731929Notes

Reaction equation

HRID 1731929 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-601e83c7534b406aa8db5c2b644c5ae1
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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