2-Chloroquinoline → HCID 19077586, compound

HRID 964604Notes

Reaction equation

HRID 964604 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].Cl[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>CN(C=O)C.[Cl-].[Na+].O>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[O:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 15376320(E)-2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methyl-acetamide

Product 1

HCID 19077586HCID 19077586, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(E)-2-[2-(hydroxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (0.44 g, 2 mmol) was dissolved in dry DMF (4 ml). 60% sodium hydride (0.10 g, 2.4 mmol) was added at room temperature, the mixture was stirred for 10 minutes, and then 2-chloroquinoline (0.36 g, 2.2 mmol) was added at room temperature. The resulting mixture was allowed to stand at room temperature overnight, and saturated brine was added. The mixture was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by column chromatography on silica gel (ethyl acetate--n-hexane) to give the title compound (0.46 g) as an oil.

Workup

  1. waitto stand at room temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting crude product was purified by column chromatography on silica gel (ethyl acetate--n-hexane)

Sources & evidence

ORD record
ord-d7f2df1d3a6846bb81c00d5dbac610f9
Source dataset
uspto-grants-1998_06
Patent number
US05770614

Reaction notes

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