Phenol → HCID 57671707, compound

HRID 871985Notes

Reaction equation

HRID 871985 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[O:23][CH3:24])=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[NH:8]2.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:4]2[C:3]([CH2:2][O:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:12]3[C:7]([NH:8][C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[NH:11]3)=[CH:6][CH:5]=2)=[C:17]([O:23][CH3:24])[CH:18]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57671748HCID 57671748, compound

Product 1

HCID 57671707HCID 57671707, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-chloromethyl-7-(4-fluoro-2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 4-1, 47.1 mg, 0.14 mmol), phenol (37.5 mg, 0.40 mmol), and potassium carbonate (73.0 mg, 0.53 mmol) was suspended in anhydrous N,N-dimethylformamide (1.5 mL) and stirred at 80° C. for 19 hours. After cooling down, ethyl acetate (30 mL) and water (30 mL) were added to the reaction mixture and partitioned. The organic layer was washed with water (30 mL) and saturated brine (30 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 compound (35.7 mg) as a pale yellow solid. (Yield 67%)

Workup

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (30 mL) and saturated brine (30 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-bf8923b2c95f4946bc8413a1274488e7
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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