Hydrogen Cyanide → 6-Chloroquinoxaline-2,3-diamine

HRID 1581126Notes

Reaction equation

HRID 1581126 reaction equation
[N:1]#[C:2][C:3]#[N:4].C#N.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([NH2:15])[CH:9]=1.[OH-].[Na+]>CO>[Cl:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:12][CH:13]=1)[N:14]=[C:2]([NH2:1])[C:3]([NH2:4])=[N:15]2

Participants

6

Reactant 4

HCID 768Hydrogen CyanideHCID 72634-Chloro-1,2-diaminobenzeneHCID 9999CyanogenHCID 14798Sodium Hydroxide

Product 1

HCID 125173906-Chloroquinoxaline-2,3-diamineYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

60 G (1.15 moles of cyanogen, which had beforehand been freed of adhering hydrocyanic acid by washing with a silver nitrate solution containing nitric acid and had been condensed in a cold trap, were passed at room temperature into a solution of 71.3 g (0.5 mole) of 1-chloro-3,4-diaminobenzene and 2 ml of 10% strength sodium hydroxide solution in 200 ml of anhydrous methanol. The reaction mixture was left to stand for 2 days at room temperature. Thereafter the resulting precipitate was filtered off, rinsed with a little methanol and dried. 41.6 G (representing 43% of theory) of 6-chloro-2,3-diamino-quinoxaline of melting point 290°C were obtained.

Workup

  1. washby washing with a silver nitrate solution
  2. additioncontaining nitric acid
  3. customcondensed in a cold trap
  4. waitThe reaction mixture was left
  5. filtrationThereafter the resulting precipitate was filtered off
  6. washrinsed with a little methanol
  7. customdried

Sources & evidence

ORD record
ord-c9ca7d903501496e997c5cc83d84c1a7
Source dataset
uspto-grants-1976_01
Patent number
US03935312

Reaction notes

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