Nitric Acid → HCID 178514504, compound

HRID 345399Notes

Reaction equation

HRID 345399 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([OH:19])[C:12]([OH:20])=[N:11]2)=[N+:6]=[N-:7].[K+].[Br-]>>[N:5]([C:8]1[C:9]([N+:1]([O-:4])=[O:2])=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([OH:19])[C:12]([OH:20])=[N:11]2)=[N+:6]=[N-:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 253877Potassium BromideHCID 178514477HCID 178514477, compound

Product 1

HCID 178514504HCID 178514504, compound

Conditions

Temperature
0 °C

Procedure

15 ml 89% nitric acid was ice-cooled and then gradually added 1 g (4,2 mmol) 6-azido-7-chloro-2,3-dihydroxyquinoxaline. After stirring at 0° C. for 15 min, the reaction mixture was poured into 100 ml ice-water. The crude product was recrystallized (acetone-methanol-water) to give 0,95 g (80%) 6-azido-7-chloro-2,3-dihydroxy-5-nitroquinooxaline. IR (KBr): 2450 cm-1 (N3). NMR (DMSO-d6) 12.3 (2H, broad s), 7.07 (1H,s).

Workup

  1. temperaturecooled
  2. customThe crude product was recrystallized (acetone-methanol-water)
  3. customto give 0,95 g (80%) 6-azido-7-chloro-2,3-dihydroxy-5-nitroquinooxaline

Sources & evidence

ORD record
ord-4cf201a4ffc74e3ba0342e324ca48ef1
Source dataset
uspto-grants-1991_10
Patent number
US05057516

Reaction notes

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