Bromine → 5-Bromo-8-ethoxalylaminoquinoline

HRID 48229Notes

Reaction equation

HRID 48229 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=[O:17])[NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)[CH3:2].[Br:19]Br>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([Br:19])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 10421911Acetic acid, oxo(8-quinolinylamino)-, ethyl ester

Product 1

HCID 47744235-Bromo-8-ethoxalylaminoquinolineYield 88.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of the product from Example 81 (20 g, 82 mmol) in 200 mL acetic acid was treated with a solution of bromine (15.7 g, 0.198 mol) in 50 mL of acetic acid and stirred at room temperature for 1 hour. The solid was collected by filtration and washed with ether to give the title compound (23.5 g, 69% yield).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-71bba429e0e8404387f2859a3b786732
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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