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Methyl iodide → 7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038478
Notes
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Reaction equation

HRID 1038478 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:8]2[C:17]([CH2:18][OH:19])=[C:16]3[C:11]([NH:12][C:13]([CH3:23])([CH3:22])[C:14](=[O:21])[N:15]3[CH3:20])=[CH:10][CH:9]=2)[CH:7]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:27])=[C:6]([C:8]2[C:17]([CH2:18][OH:19])=[C:16]3[C:11]([NH:12][C:13]([CH3:22])([CH3:23])[C:14](=[O:21])[N:15]3[CH3:20])=[CH:10][CH:9]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 247808507-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576717857-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 96.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-(5-chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 12-1, 1.36 g, 3.92 mmol), methyl iodide (244 μL, 3.92 mmol), and potassium carbonate (1.08 g, 7.81 mmol) was suspended in anhydrous N,N-dimethylformamide (20 mL) and stirred at 50° C. for 1 hour. After cooling down, ethyl acetate (70 mL), diethylether (70 mL), and water (150 mL) were added and partitioned. The organic layer was washed with water (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.36 g) as a pale yellow amorphous product. (Yield 96%)

Workup

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (100 mL) and saturated brine (50 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7fbbe91bc6874ab680f36f08b3642642
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551991B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes