Sodium Hydroxide → HCID 25096967, compound

HRID 215677Notes

Reaction equation

HRID 215677 reaction equation
[Sn](Cl)Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:25].[OH-].[Na+]>C(O)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 25096725HCID 25096725, compound

Product 1

HCID 25096967HCID 25096967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (3.32 g, 17.5 mmol) was slowly added to an ethanol solution (30 ml) that contained compound 23 (520 mg, 1.75 mmol), while stirring. The obtained mixture was heated to reflux for 1 hour. After completion of the reaction, a 1 N sodium hydroxide aqueous solution (150 ml) was added to the reaction solution, and the obtained mixture was then extracted with 50 ml of ethyl acetate (150 ml). The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure, so as to obtain a product of interest, 6-methoxy-4′-aminoflavone (compound 24) in the form of a yellow crystal. Yield: 360 mg (yield constant: 74.8%) 1H NMR (300 MHz, DMSO-d6) δ7.91 (d, J=8.7 Hz, 2H), 7.69-7.70 (m, 1H), 7.38-7.42 (m, 2H), 6.93 (d, J=9.0 Hz, 2H), 6.82 (s, 1H), 3.86 (s, 2H).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureto reflux for 1 hour
  3. customAfter completion of the reaction
  4. extractionthe obtained mixture was then extracted with 50 ml of ethyl acetate (150 ml)
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled away under reduced pressure

Sources & evidence

ORD record
ord-62c22f3a95144fef8acb7e54e6623173
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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