Hydrochloric Acid → HCID 9992548, compound

HRID 1600748Notes

Reaction equation

HRID 1600748 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([C:14]#[N:15])[C:3]=1[Cl:16].N([O-])=O.[Na+].N#N.[ClH:23]>O.Cl[Cu]>[C:14]([C:4]1[C:3]([Cl:16])=[C:2]([Cl:23])[CH:11]=[C:10]2[C:5]=1[NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)#[N:15]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 947NitrogenHCID 23668193Sodium NitriteHCID 53974344HCID 53974344, compound

Product 1

HCID 9992548HCID 9992548, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent3×

Procedure

To a stirred solution of 7-amino-6-chloro-5-cyanoquinoxaline-2(1H),3(4H)-dione (0.035 g, 0.15 mmol, as prepared above) in concentrated HCl (1.5 mL) at 0° C., an aqueous solution of NaNO2 (0.060 g, 0.87 mmol) in water (0.20 mL) was added and the resulting turbid solution was stirred in an ice bath for 2 h. A solution of CuCl (0.100 g, 1.01 mmol) in concentrated HCl (1.0 mL) was added to it while cooling the flask in an ice bath. Instant evolution of N2 ensued and the resulting dark green suspension was stirred at 0° C. for 2 h. Water (1.0 mL) was added to it followed by stirring overnight at room temperature. To the light green suspension so formed, water (4.0 mL) was added with further stirring at room temperature for 1 h. The precipitated solid was filtered, washed with water (2.0 mL), and dried under vacuum to furnish 0.029 g (77%) of the title compound as a cream colored solid; m. p. 327-335° C. (decomposed); 1H NMR (DMSO-d6): δ 7.463 (d, 1H, J=1.2 Hz), 12.306 (s, 2H). The coupling of aromatic signal disappeared upon addition of 3 drops of methanol-d4 indicating that the aromatic proton had coupled with peri N--H proton; IR (KBr, cm-1); 3574, 3479, 2237, 1737, 1710, 1392, 1271, 1183.

Workup

  1. temperaturewhile cooling the flask in an ice bath
  2. stirringthe resulting dark green suspension was stirred at 0° C. for 2 h
  3. stirringby stirring overnight at room temperature
  4. customTo the light green suspension so formed
  5. stirringwith further stirring at room temperature for 1 h
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water (2.0 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-c53966eeb7d94a4d9d7da1b28ee4e182
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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