Dimethylformamide → 8-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-2-methylquinoline

HRID 564929Notes

Reaction equation

HRID 564929 reaction equation
[Cl:1][C:2]1[C:20]([NH:21][C:22](=[O:35])[CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])=[CH:19][CH:18]=[C:17]([Cl:36])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.[CH3:37]N(C)C=O.[H-].[Na+].CI>O>[Cl:1][C:2]1[C:20]([N:21]([C:22](=[O:35])[CH2:23][N:24]2[C:25](=[O:34])[C:26]3=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]3[C:28]2=[O:29])[CH3:37])=[CH:19][CH:18]=[C:17]([Cl:36])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 105061448-[2,6-Dichloro-3-(phthalimidoacetylamino)benzyloxy]-2-methylquinoline

Product 1

HCID 118004498-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 8-[2,6-dichloro-3-(phthalimidoacetylamino)benzyloxy]-2-methylquinoline (4.44 g) and N,N-dimethylformamide (44 ml) was added sodium hydride (60% in oil, 375 mg) in an ice-water bath. After stirring for 30 minutes in an ice-water bath, methyl iodide (0.6 ml) was added thereto and the mixture was stirred at ambient temperature for 1 hour. To this mixture was added, water (88 ml) in an ice-water bath and the mixture was stirred at the same temperature for 1.5 hours. The precipitate was collected by vacuum filtration and washed with water and methanol to give 8-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-2-methylquinoline (3.99 g) as a yellow powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. additionTo this mixture was added
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-49454dbacb6a4b6ba63f2e30cb9b5dd1
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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