Benzoyl chloride → 8-Benzoyloxymethyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871983Notes

Reaction equation

HRID 871983 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[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(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C>O1CCCC1.O>[C:31]([O:1][CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]([CH3:14])([CH3:15])[NH:8]2)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 247808478-Hydroxymethyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576717398-Benzoyloxymethyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-Hydroxymethyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 3-1, 54.2 mg, 0.17 mmol) was dissolved in tetrahydrofuran (1.5 mL) and triethylamine (73.0 μL, 0.52 mmol) and benzoyl chloride (30.0 μL, 0.26 mmol) were added thereto successively. The reaction mixture was stirred at room temperature for 24 hours. 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 filtered with ethyl acetate to give the titled compound (54.1 mg) as a colorless solid. (Yield 76%)

Workup

  1. custompartitioned
  2. washThe organic layer was washed with water (30 mL) and saturated brine (30 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. filtrationThe obtained residue was filtered with ethyl acetate

Sources & evidence

ORD record
ord-0466d1a4fe9a450da7d376d7cd9b02ad
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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