Chloromethyl Methyl Ether → HCID 22499174, compound

HRID 2089073Notes

Reaction equation

HRID 2089073 reaction equation
[CH3:1][O:2][CH2:3]Cl.C(=O)([O-])[O-].[K+].[K+].[Br:11][C:12]1[C:21]([CH3:22])=[CH:20][C:19]([OH:23])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:24])[NH:17]2>CN(C)C=O>[Br:11][C:12]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH2:1][O:2][CH3:3])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:24])[NH:17]2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 22499224HCID 22499224, compound

Product 1

HCID 22499174HCID 22499174, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methoxymethyl chloride (410 μL) was added to a suspension of potassium carbonate (1.24 g) in a solution of 5-bromo-8-hydroxy-6-methyl-1H-quinolin-2-one (480 mg) in dimethylformamide (9 mL) at 0° C. The reaction mixture is stirred for 18 hours at room temperature, filtered, the solvent removed in vacuo, and the product purified by flash column chromatography on silica gel, eluting with 2% methanol in dichloromethane.

Workup

  1. filtrationfiltered
  2. customthe solvent removed in vacuo
  3. customthe product purified by flash column chromatography on silica gel
  4. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-a2d2619d57594f8ebc24ace90ae4caa4
Source dataset
uspto-grants-2013_05
Patent number
US08436017B2

Reaction notes

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