Triethylamine → HCID 69517315, compound

HRID 1831227Notes

Reaction equation

HRID 1831227 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[I-].C[N+]1C=CN([C:19](=[O:28])[N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)C=1.C(N(CC)CC)C>C(#N)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][C:19](=[O:28])[N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodideHCID 178516385quinolin-4-ol

Product 1

HCID 69517315HCID 69517315, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxyquinoline (0.44 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 (50:50)) yielding the title compound (0.75 g, 90% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50))

Sources & evidence

ORD record
ord-6757e8504b5940aa968cdc483b28b558
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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