Hydrochloric Acid → 8-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038496Notes

Reaction equation

HRID 1038496 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]([CH2:26][O:27][C:28]3[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=3[CH3:35])=[C:24]3[C:19]([NH:20][C:21]([CH3:39])([CH3:38])[C:22](=[O:37])[N:23]3[CH3:36])=[CH:18][CH:17]=2)=[C:12]([O:40][CH3:41])[CH:11]=1)(=O)C1C=CC=CC=1.O.Cl>CO.O1CCCC1.[OH-].[Na+]>[F:34][C:32]1[CH:31]=[CH:30][C:29]([CH3:35])=[C:28]([CH:33]=1)[O:27][CH2:26][C:25]1[C:16]([C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][C:12]=2[O:40][CH3:41])=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]([CH3:36])[C:22](=[O:37])[C:21]([CH3:39])([CH3:38])[NH:20]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 576718857-(4-Benzoyloxy-2-methoxyphenyl)-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 252112638-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

7-(4-Benzoyloxy-2-methoxyphenyl)-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 6-31, 422 mg, 0.761 mmol) was dissolved in mixed solvent of methanol (2 mL) and tetrahydrofuran (2 mL), and 4N aqueous sodium hydroxide solution (0.761 mL, 3.04 mmoL) was added thereto. After the reaction mixture was stirred at room temperature for 40 minutes, water (100 mL) and 1N aqueous HCl solution (4 mL) were added thereto. After the mixture was extracted with ethyl acetate mL), the organic layer was washed with water 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 filtered with a mixed solvent of hexane (10 mL) and ethyl acetate (10 mL) to give the titled compound (292 mg) as a colorless solid. (Yield 85%)

Workup

  1. additionwas added
  2. extractionAfter the mixture was extracted with ethyl acetate mL), the organic layer
  3. washwas washed with water mL) and saturated brine (50 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationThe obtained residue was filtered with a mixed solvent of hexane (10 mL) and ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-7b27528a978f4a3db86a20b8e815301e
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

Loading…