Benzyl Bromide → Oxo [(phenylmethyl)(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)amino]acetic Acid Ethyl Ester

HRID 48237Notes

Reaction equation

HRID 48237 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].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[C:5](=[O:6])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[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)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10334564[(1,2,3,4-Tetrahydro-6-nitro-5-quinolinyl)amino]oxo-acetic Acid Ethyl Ester

Product 1

HCID 57199892Oxo [(phenylmethyl)(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)amino]acetic Acid Ethyl EsterYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product from Example 87 (0.58 g, 2 mmol), benzylbromide (0.41 g, 2.4 mmol) and cesium carbonate (0.78 g, 2.4 mmol) in 10 mL of acetonitrile was stirred at room temperature for 2 hours. The triethylamine hydrobromide was removed by filtration and the filtrate evaporated. The residue was purified by silica gel chromatography (2:1 heptane:ethyl acetate as eluant) to give the title compound as a yellow solid (0.7 g, 91% yield).

Workup

  1. customThe triethylamine hydrobromide was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was purified by silica gel chromatography (2:1 heptane:ethyl acetate as eluant)

Sources & evidence

ORD record
ord-78d2979351614d528fc245cf82d1e470
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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