Sodium Hydroxide → HCID 59389311, compound

HRID 2357950Notes

Reaction equation

HRID 2357950 reaction equation
[OH-:1].[Na+].[CH2:3]([C:5]1[CH:17]=[C:8]2[C:9]([CH:15]=[O:16])=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[N:7]2[N:6]=1)[CH3:4]>[N+]([O-])([O-])=O.[Ag+]>[CH2:3]([C:5]1[CH:17]=[C:8]2[C:9]([C:15]([OH:1])=[O:16])=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[N:7]2[N:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59389353HCID 59389353, compound

Product 1

HCID 59389311HCID 59389311, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

An aqueous suspension (526 mL) of silver nitrate (22.28 g) and sodium hydroxide (10.86 g, 15.1) was added to the compound of Example 347 (10.76 g). The mixture was stirred at room temperature for 1.5 hours. Subsequently, the insoluble material in the mixture was removed by filtration through Celite. The filtrate was washed with diethyl ether. Diluted hydrochloric acid was then added to the aqueous layer to make it acidic. The mixture was then extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as a yellow powder (11.13 g).

Workup

  1. customSubsequently, the insoluble material in the mixture was removed by filtration through Celite
  2. washThe filtrate was washed with diethyl ether
  3. additionDiluted hydrochloric acid was then added to the aqueous layer
  4. extractionThe mixture was then extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-521e76c777b743f4ac94cd27c7cc9903
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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