Triethylamine → 7-Chloro-4-quinolinyl methyl(phenyl)carbamate

HRID 1179850Notes

Reaction equation

HRID 1179850 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[I-].C[N+]1C=CN([C:20](=[O:29])[N:21]([CH3:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)C=1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:20](=[O:29])[N:21]([CH3:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodideHCID 178516426HCID 178516426, compound

Product 1

HCID 7497907-Chloro-4-quinolinyl methyl(phenyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-chloro-4-hydroxyquinoline (0.54 g, 3.00 mmol), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in acetonitrile (15 ml) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (40:60)) yielding the title compound (0.87 g, 93% yield) as a colourless oil which solidified upon standing.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (40:60))

Sources & evidence

ORD record
ord-99aae05660524676adccca37a4b4483a
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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