Sodium Bicarbonate → HCID 178439263, compound

HRID 1023919Notes

Reaction equation

HRID 1023919 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[OH:18])=[CH:4][CH:3]=1.N([O-])=[O:20].[Na+].C([O-])(O)=O.[Na+]>OS(O)(=O)=O.O.[O-]S([O-])(=O)=O.[Cu+2]>[OH:18][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][CH3:17])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:4]=[CH:3][C:2]([OH:20])=[N:7][CH:6]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 59191233HCID 59191233, compound

Product 1

HCID 178439263HCID 178439263, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-[(6-aminopyridin-3-yl)oxy]-5-propylphenol (0.20 mmol; 50 mg) under argon, in H2SO4 (35%; 0.2 mL), cooled to 0° C., was slowly added NaNO2 (0.26 mmol; 18 mg) in water (0.2 mL). After 30 min, CuSO4 (3 mmol; 477 mg) in water (1 mL), then Cu2O (0.18 mmol; 26 mg) were added. After 30 min, the mixture was neutralised with NaHCO3 sat. (1 mL), extracted with ethyl acetate (3*3 mL). Combined organic phases were washed with water (3 mL), dried over MgSO4, concentrated in vacuo. An analytical sample was obtained by preparative TLC to yield the title compound as a white solid (5 mg; 0.02 mmol; ca 20%).

Workup

  1. waitAfter 30 min
  2. extractionextracted with ethyl acetate (3*3 mL)
  3. washCombined organic phases were washed with water (3 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customAn analytical sample was obtained by preparative TLC

Sources & evidence

ORD record
ord-2da66883be5444608917728811412ecd
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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