Sodium Hydroxide → HCID 59334623, compound

HRID 1639740Notes

Reaction equation

HRID 1639740 reaction equation
[N+:1]([C:4]1C=C([N+]([O-])=O)C=C[C:5]=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1.[OH-].[Na+]>C(#N)C>[CH3:5][C:4]1[N:1]=[C:16]2[C:17]([CH2:21][OH:22])=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866419191-Amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate

Product 1

HCID 59334623HCID 59334623, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate (100 g, 323 mmol) in acetonitrile (1.08 L), was added 2 N sodium hydroxide (485 mL) at room temperature, and the mixture was stirred for 12 hr. Acetonitrile was evaporated under reduced pressure, and the residual aqueous solution was extracted with 3 times with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (14.0 g, yield 29%).

Workup

  1. customAcetonitrile was evaporated under reduced pressure
  2. extractionthe residual aqueous solution was extracted with 3 times with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bdf46ed98c9c446f8c8f067321182f2f
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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