Sodium Hydroxide → HCID 11275999, compound

HRID 2298999Notes

Reaction equation

HRID 2298999 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1)([CH3:3])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[Na+]>OS(O)(=O)=O>[CH:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[CH2:7][CH2:6][N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 12490810HCID 12490810, compound

Product 1

HCID 11275999HCID 11275999, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of Example 13F (0.73 g, 4.2 mmol) in concentrated H2SO4 (7.5 mL) at 0° C. was treated with KNO3 (0.47 g, 4.6 mmol), stirred for 30 minutes, treated with ice water, adjusted to pH>7 with 25% NaOH, and extracted with dichloromethane. The combined extracts were washed with H2O and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c25cdaa415164f9a90b8aaf5cb586cb8
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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