Water → HCID 68867939, compound

HRID 729989Notes

Reaction equation

HRID 729989 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:6]=1.C([O-])(O)=[O:25].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+].[O-]S([O-])=O.[Na+].[Na+].[OH2:47]>CC(C)=O>[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][NH:4][C:5]1[N:6]=[C:7]([C:14](=[O:25])[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:47])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

8

Reactant 6

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 68866633HCID 68866633, compound

Product 1

HCID 68867939HCID 68867939, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Cool a mixture of (2,2-dimethylpropyl)-(3-nitro-6-phenylethynylpyridin-2-yl)amine (3.11 g, 10 mmol), NaHCO3 (0.420 g, 5.0 mmol), MgSO4 (2.40 g, 20 mmol) in acetone (85 mL), and water (25 mL) and cool to 0° C. Add KMnO4 (3.16 g, 20.0 mmol) to the cooled mixture, and stir the reaction mixture vigorously at 0° C. for about 1-2 h. Quench the mixture with Na2SO3 (5.67 g, 45 mmol). Remove ice bath and stir mixture at RT for 2 h. Filter the solid through a pad of filtering agent. Wash with water (2×50 mL) and EtOAc (50 mL). Separate the phases and extract the aqueous phase with EtOAc (3×50 mL). Wash the combined organic phases with saturated aqueous NaCl (25 mL), dry with MgSO4, filter and concentrate. Purify the crude (silica gel chromatography, eluting with 1:1 hexanes:CH2Cl2) to give the title compound (1.586 g, 46%).

Workup

  1. temperatureCool
  2. filtrationFilter the solid through a pad
  3. filtrationof filtering agent
  4. washWash with water (2×50 mL) and EtOAc (50 mL)
  5. customSeparate the phases
  6. extractionextract the aqueous phase with EtOAc (3×50 mL)
  7. washWash the combined organic phases with saturated aqueous NaCl (25 mL)
  8. dry with materialdry with MgSO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify
  12. washthe crude (silica gel chromatography, eluting with 1:1 hexanes:CH2Cl2)

Sources & evidence

ORD record
ord-df8176eabdd6475282a17740051a0b6c
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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