Water → HCID 54006413, compound

HRID 2287460Notes

Reaction equation

HRID 2287460 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:23])[C:9](=[O:22])[CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[CH:6][CH:5]=[C:4]([Cl:24])[C:3]=1[CH2:25][O:26]S(C)(=O)=O.O[C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[C:39]([CH3:42])[CH:38]=[C:37]2[N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]([C:9](=[O:22])[CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[CH3:23])=[CH:6][CH:5]=[C:4]([Cl:24])[C:3]=1[CH2:25][O:26][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[C:39]([CH3:42])[CH:38]=[C:37]2[N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 184042364-(1H-Imidazol-1-yl)-2-methylquinolin-8-olHCID 212546862,6-dichloro-3-[N-methyl-N-(phthalimidoacetyl)amino]benzyl methanesulfonate

Product 1

HCID 54006413HCID 54006413, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,6-dichloro-1-mesyloxymethyl-3-(N-methyl-N-phthalimidoacetylamino)benzene (2.35 g), tetrabutylammonium iodide (123 mg) and molecular sieves 4A (340 mg) in N,N-dimethylformamide (38 ml) were added 8-hydroxy-4-(imidazol-1-yl)-2-methylquinoline (750 mg) and potassium carbonate (2.3 g) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature and overnight at ambient temperature. Water and chloroform were added thereto, and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized with ethyl acetate to give 8-[2,6-dichloro-3-(N-phthalimidoacetyl-N-methylamino)benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (1.92 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. washthe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-e05f29fbd94d47bc864f6afd56fece7e
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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