Stannous Chloride → HCID 69507304, compound

HRID 1768454Notes

Reaction equation

HRID 1768454 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2[O:30][CH3:31])=[CH:7][CH:8]=[C:9]([NH:14][C:15]([C:18](OC)=[O:19])([CH3:17])[CH3:16])[C:10]=1[N+:11]([O-])=O)=[O:4].[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]2[NH:11][C:18](=[O:19])[C:15]([CH3:16])([CH3:17])[NH:14][C:9]=2[CH:8]=[CH:7][C:6]=1[C:22]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=1[O:30][CH3:31])=[O:4]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 58891825HCID 58891825, compound

Product 1

HCID 69507304HCID 69507304, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of biphenyl vi (800 mg, 1.85 mmol) in EtOH (20 mL) was added tin(II) chloride (1.76 g, 9.26 mmol). The mixture was heated at reflux for 16 h and then cooled to room temperature. The reaction mixture was diluted with EtOAc (50 mL) and basified with saturated aqueous NaHCO3. The resulting white suspension was stirred at room temperature for 30 min, then filtered through celite and the precipitate was washed by EtOAc (3×20 mL). The two layers were separated and the organic layer was collected. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine and dried over MgSO4. After the solvent was removed under reduced pressure, the residue was purified by flash chromatography (EtOAc/hexane, 40% to 70%) to yield vii as a light yellow solid (500 mg, 73%). 1H NMR (CDCl3): δ 7.93 (br s, 1H), 7.14 (t, J=8.4 Hz, 1H), 6.73 (m, 2H), 6.51 (d, J=8.4 Hz, 1H), 3.62 (s, 6H), 3.37 (s, 3H), 1.34 (s, 6H). Anal. Calcd for C20H22N2O5: C, 64.85; H, 5.99; N, 7.56. Found: C, 65.00; H, 5.73; N, 7.31.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered through celite
  4. washthe precipitate was washed by EtOAc (3×20 mL)
  5. customThe two layers were separated
  6. customthe organic layer was collected
  7. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. customAfter the solvent was removed under reduced pressure
  11. customthe residue was purified by flash chromatography (EtOAc/hexane, 40% to 70%)

Sources & evidence

ORD record
ord-654f94029b1a4cb8a53c89dc813edd92
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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