Water → HCID 178448683, compound

HRID 1377416Notes

Reaction equation

HRID 1377416 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].[C:8]([O-:11])(=O)[CH3:9].[Na+].O>C(O)C>[CH2:6]([N:1]1[C:8]([OH:11])=[CH:9][C:4]([CH3:5])=[C:3]([C:2]#[N:1])[C:2]1=[O:7])[CH2:5][CH2:4][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 88712-PyridoneHCID 517045Sodium Acetate

Product 1

HCID 178448683HCID 178448683, compoundYield 239.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1.0 grams (4.85 mmol) of the pyridone and 6.6 grams (48.5 mmol, 10 eq) of sodium acetate in 50 mL of ethanol was added 1.27 grams (4.85 mmol, 1 eq) of 4-diazo-N,N'-diethylaniline tetrafluoroborate. The reaction mixture turned blue immediately upon addition of the diazo compound. The mixture was stirred at room temperature for two hours and 50 mL of water was added. The blue solid was collected and washed with water and dried. This material was recrystallized from approximately 200 mL of ethanol to give 1.2 grams (65% yield) of the desired product. This material decomposes at 180°-185° C. with effervescence.

Workup

  1. customThe blue solid was collected
  2. washwashed with water
  3. customdried
  4. customThis material was recrystallized from approximately 200 mL of ethanol

Sources & evidence

ORD record
ord-7a8cb8826ec146278f240d7fb6a57ef0
Source dataset
uspto-grants-1997_09
Patent number
US05665522

Reaction notes

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