N-bromobutanimide → [(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl Ester

HRID 48241Notes

Reaction equation

HRID 48241 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2].[Br:22]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:22])=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10334564[(1,2,3,4-Tetrahydro-6-nitro-5-quinolinyl)amino]oxo-acetic Acid Ethyl Ester

Product 1

HCID 10474405[(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl EsterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Example 87 (0.15 g, 0.5 mmol) and N-bromosuccinimide (0.23 g, 1 mmol) in 2 mL dimethylformamide was stirred at room temperature for 18 hours. The solution was poured onto methylene chloride/water and separated and the water layer back extracted with methylene chloride. The combined organic layers were washed with water, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant) to give the title compound (0.15 g, 81% yield).

Workup

  1. additionThe solution was poured onto methylene chloride/water
  2. customseparated
  3. extractionthe water layer back extracted with methylene chloride
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant)

Sources & evidence

ORD record
ord-4371e4c6c5364e52a692bc88fa9d0ae1
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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