Nitric Acid → 5-Bromo-8-ethoxalylamino-7-nitroquinoline

HRID 48230Notes

Reaction equation

HRID 48230 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([Br:18])=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:6])[CH3:2].[N+:20]([O-])([OH:22])=[O:21]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:19])[C:5]([NH:7][C:8]1[C:9]([N+:20]([O-:22])=[O:21])=[CH:10][C:11]([Br:18])=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 47744235-Bromo-8-ethoxalylaminoquinoline

Product 1

HCID 117264985-Bromo-8-ethoxalylamino-7-nitroquinolineYield 45%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Example 82 (23.5 g, 58 mmol) in 30 mL fuming nitric acid and 150 mL trifluoroacetic acid was heated at 80° C. for 18 hours. The solvent was removed and the residue was treated with water to give a solid. The solid was collected by filtration and washed with ether and dried to give the title compound (9.5 g, 45% yield).

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with water
  3. customto give a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-a9da6a8a18414bbcb6b8c0cdc89508a7
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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