Chloromethyl Methyl Ether → HCID 22344490, compound

HRID 583833Notes

Reaction equation

HRID 583833 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[H-].[Na+].[CH3:14][O:15][CH2:16]Cl>CN(C)C=O.O>[CH3:14][O:15][CH2:16][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 135441757Quinolin-5-ol

Product 1

HCID 22344490HCID 22344490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-hydroxyquinoline (10.3 g) in dimethylformamide (140 ml) was ice-cooled. To the solution was added sodium hydride (3.0 g, 62.6% in oil) and the mixture was stirred at 0° C. for 15 minutes. To the reaction mixture was added methoxymethyl chloride (6.5 ml) and then the mixture was stirred at 0° C. for 2 hours. To the reaction mixture was added ice. The reaction mixture was stirred and then diluted with water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 1N aqueous solution of sodium hydroxide, water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate, and then concentrated to give the title compound (10.4 g) having the following physical data. The obtained compound was used without purification in the subsequent reaction.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. additionTo the reaction mixture was added ice
  4. stirringThe reaction mixture was stirred
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with 1N aqueous solution of sodium hydroxide, water
  7. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-eb92906ba67249478cf23ad9a29a6cc8
Source dataset
uspto-grants-2005_08
Patent number
US06924295B2

Reaction notes

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