Methyl iodide → [Methyl(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl Ester

HRID 48239Notes

Reaction equation

HRID 48239 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].CI.[C:24](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]([N:7]([CH3:24])[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]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 10334564[(1,2,3,4-Tetrahydro-6-nitro-5-quinolinyl)amino]oxo-acetic Acid Ethyl Ester

Product 1

HCID 69893668[Methyl(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl EsterYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product from Example 87 (0.87 g, 3 mmol), methyl iodide (0.51 g, 3.6 mmol) and cesium carbonate (1.17 g, 3.6 mmol) in 15 mL of acetonitrile was stirred at room temperature for 2 hours. The inorganic salts were removed by filtration and the filtrate evaporated. The residue was dissolved in methylene chloride, filtered and evaporated. The product was then used without further purification (0.86 g, 93% yield).

Workup

  1. customThe inorganic salts were removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was then used without further purification (0.86 g, 93% yield)

Sources & evidence

ORD record
ord-eaa696314db3410aaba7442db2b4682d
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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