Imidazole → 8-(2,6-Dichlorobenzoylamino)-3-(imidazol-1-ylmethyl)quinoline

HRID 613489Notes

Reaction equation

HRID 613489 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH3:17])=[CH:12]2)=[O:5].BrN1C(=O)CCC1=O.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC(OC)(C)C)C#N.BrCC1C=[N:57][C:58]2C(C=1)=CC=C[C:59]=2[NH:65][C:66](=O)C1C(Cl)=CC=CC=1Cl.N1C=CN=C1>C(Cl)(Cl)(Cl)Cl.C(Cl)CCl>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][N:57]1[CH:58]=[CH:59][N:65]=[CH:66]1)=[CH:12]2)=[O:5]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 67184N-bromobutanimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 195923883-Bromomethyl-8-(2,6-dichlorobenzoylamino)quinolineHCID 195927078-(2,6-Dichlorobenzoylamino)-3-methylquinoline

Product 1

HCID 195926608-(2,6-Dichlorobenzoylamino)-3-(imidazol-1-ylmethyl)quinoline

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-3-methylquinoline (104 mg), N-bromosuccinimide (67.1 mg) and 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) (20.1 mg) in carbon tetrachloride (3 ml) was refluxed for 2 hours. After cooling, the mixture was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 3-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline. The residue was dissolved in ethylene chloride, and imidazole (64.1 mg) was added thereto. After stirring for 2.5 hours at 60° C., the mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane) to give 8-(2,6-dichlorobenzoylamino)-3-(imidazol-1-ylmethyl)quinoline (36.2 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. washthe mixture was washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto give a residue
  7. washthe mixture was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-08c53389d8a24d998fde806acea60354
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…