Ethanol → HCID 57671962, compound

HRID 871990Notes

Reaction equation

HRID 871990 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]=[C:27]([N+:29]([O-])=O)[CH:26]=[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.CN(C)C=O.C(O)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:29][C:27]1[CH:26]=[CH:25][C:24]([O:32][CH3:33])=[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)[CH:28]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 6228DimethylformamideHCID 57671722HCID 57671722, compound

Product 1

HCID 57671962HCID 57671962, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-(2-methoxy-5-nitrophenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 6-27, 18.8 mg, 0.0392 mmol) and tin chloride (II) (23.0 mg, 0.121 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. overnight. 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 precipitate was filtered, 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 compound (8.2 mg) as a brown solid. (Yield 47%)

Workup

  1. temperatureAfter cooling down
  2. additionwas added
  3. filtrationAfter the precipitate was filtered
  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-b086199e6e204f72a83a0ee47e418014
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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