Hydrochloric Acid → HCID 28903252, compound

HRID 2085719Notes

Reaction equation

HRID 2085719 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([NH:6][CH2:7][CH2:8][CH2:9][CH3:10])=[C:4]([N+:13]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl.Cl.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 22730366HCID 22730366, compound

Product 1

HCID 28903252HCID 28903252, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of Example 166A (1.82 g, 6.66 mmol) and tin(II) chloride dihydrate (3.76 g, 16.6 mmol), and concentrated HCl (22 mL) in isopropanol (30 mL) at room temperature was stirred for 90 minutes, adjusted to pH 6.5-7.5 using NaHCO3 and 6M NaOH, and filtered. The filter cake was washed with water and ethyl acetate, and the filtrate was separated. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic phases were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water and ethyl acetate
  3. customthe filtrate was separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  5. washthe combined organic phases were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e8016dad84fb480f94a70f28144309dd
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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