Iodoethane → HCID 58615345, compound

HRID 1295453Notes

Reaction equation

HRID 1295453 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=[C:5]2[OH:16].[CH2:17](I)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=[C:5]2[O:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178474346HCID 178474346, compound

Product 1

HCID 58615345HCID 58615345, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(6-bromo-4-hydroxy-quinolin-2-yl)-acetamide (32 g, 0.114 mol), ethyl iodide (26.77 g, 0.171 mol) and potassium carbonate (130 g, 0.912 mol) in acetonitrile (250 ml) was refluxed for 2 h. The solvent was evaporated and the residue was triturated with water. The precipitate was collected by filtration and dried to afford N-(6-bromo-4-ethoxy-quinolin-2-yl)-acetamide as a pale yellow solid (28 g, 80%). This material was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was triturated with water
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-57c9c55e88e2421d84c6e1165077b2ae
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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