Methyl iodide → HCID 15035217, compound

HRID 1656433Notes

Reaction equation

HRID 1656433 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)(=[O:3])[CH3:2].[H-].[Na+].[CH3:24]I>CN(C)C=O.O>[Cl:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([N:4]([CH3:24])[C:1](=[O:3])[CH3:2])=[C:14]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10424681HCID 10424681, compound

Product 1

HCID 15035217HCID 15035217, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-acetamido-6-chloro-4-phenylquinoline (1 g) in N,N-dimethylformamide (10 ml) was added 60% sodium hydride in oil (0.15 g). After stirring for 30 mins. at room temperature, to the mixture was added dropwise methyl iodide(0.25 ml) under stirring and then followed by stirring for 1 hr. at room temperature. After the mixture was diluted with water, the resultant precipitate was collected by filtration, and recrystallized from a mixture of methanol and chloroform to give 6-chloro-3-(N-methylacetamido)-4-phenylquinoline as colorless crystals. Yield 0.96 g (91.4%). m.p. 268°-270° C.

Workup

  1. stirringunder stirring
  2. stirringby stirring for 1 hr
  3. customat room temperature
  4. filtrationthe resultant precipitate was collected by filtration
  5. customrecrystallized from a mixture of methanol and chloroform

Sources & evidence

ORD record
ord-3912a3fff38a40dcadbae4b9b935c394
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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