Ethanol → HCID 57671828, compound

HRID 215822Notes

Reaction equation

HRID 215822 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:35])=[C:6]([CH:34]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:24]=2[O:32][CH3:33])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.[Sn](Cl)(Cl)(Cl)Cl.CN(C)C=O.C(O)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([C:10]2[C:9]([CH2:8][O:7][C:6]3[CH:34]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:35])=[C:18]3[C:13]([NH:14][C:15]([CH3:22])([CH3:21])[C:16](=[O:20])[N:17]3[CH3:19])=[CH:12][CH:11]=2)=[C:24]([O:32][CH3:33])[CH:25]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 24287Tin tetrachlorideHCID 57671882HCID 57671882, compound

Product 1

HCID 57671828HCID 57671828, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-(2-methoxy-4-nitrophenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 8-6, 26.1 mg, 0.0544 mmol) and tin chloride (II) (64.8 mg, 0.342 mmol) was suspended in mixed solvent of anhydrous N,N-dimethylformamide (0.25 ml) and anhydrous ethanol (0.5 mL), and stirred at 80° C. for 3 days. After cooling down, the reaction mixture was diluted with ethyl acetate (10 mL) and saturated aqueous sodium hydrogen carbonate solution was added thereto until the pH became 9. After the precipitated solids were filtered out, the filtrate was washed with water (50 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 (12.1 mg) as a brown solid. (Yield 50%)

Workup

  1. temperatureAfter cooling down
  2. additionwas added
  3. filtrationAfter the precipitated solids were filtered out
  4. washthe filtrate was washed with water (50 mL) and saturated brine (50 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-160922c057874261946ab165bebf45d6
Source dataset
uspto-grants-2012_06
Patent number
US08193187B2

Reaction notes

Loading…