Triethylamine → 8-Hydroxymethyl-7-[2-methoxy-4-(2-methylbenzoyloxy)phenyl]-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871981Notes

Reaction equation

HRID 871981 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([CH2:18][OH:19])=[C:16]3[C:11]([NH:12][C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[NH:15]3)=[CH:10][CH:9]=2)=[C:4]([O:23][CH3:24])[CH:3]=1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>O1CCCC1.C(OCC)(=O)C>[OH:19][CH2:18][C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[CH3:32])=[CH:3][C:4]=2[O:23][CH3:24])=[CH:9][CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:20])[C:13]([CH3:21])([CH3:22])[NH:12]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 576719857-(4-Hydroxy-2-methoxyphenyl)-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 689266918-Hydroxymethyl-7-[2-methoxy-4-(2-methylbenzoyloxy)phenyl]-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-(4-Hydroxy-2-methoxyphenyl)-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 3-5, 430 mg, 1.31 mmol) was dissolved in tetrahydrofuran (10 mL), and triethylamine (365 μL, 2.62 mmol) and 2-methylbenzoyl chloride (222 μL, 1.70 mmol) were added thereto successively. After the reaction mixture was stirred at the same temperature for 80 minutes, the reaction mixture was diluted with ethyl acetate (200 mL). The mixture was washed with water (100 mL) and saturated brine (100 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 (362 mg) as a colorless solid. (Yield 62%)

Workup

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

Sources & evidence

ORD record
ord-084bca3ecc67474194e87615a2a8432d
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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