Nitric Acid → HCID 178526902, compound

HRID 711388Notes

Reaction equation

HRID 711388 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2[OH:12].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][C:6]([N+:13]([O-:15])=[O:14])=[C:5]2[OH:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178516799HCID 178516799, compound

Product 1

HCID 178526902HCID 178526902, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

Under N2, an orange solution of 6-bromocinnolin-4-ol (18.5 g, 82 mmol) in HNO3 (90 mL, 82 mmol) was cooled to 0° C., and H2SO4 (30 mL) was added. The resulting mixture was then heated at 60° C. for 3 h. After the reaction went to completion as monitored by LC-MS, the reaction mixture was cooled to 0° C., and was then quenched with H2O (20 mL). The mixture was diluted with EtOAc (25 mL). Following general workup procedures, the crude residue was added to silica gel, and eluted with PE/EtOAc to give 6-bromo-3-nitrocinnolin-4-ol as a pale yellow solid (13 g, yield 58.6%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customwas then quenched with H2O (20 mL)
  3. additionThe mixture was diluted with EtOAc (25 mL)
  4. additionthe crude residue was added to silica gel
  5. washeluted with PE/EtOAc

Sources & evidence

ORD record
ord-6613bd8186a44a66924a673a51be96cd
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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