Acetic Acid → HCID 178493295, compound

HRID 2416688Notes

Reaction equation

HRID 2416688 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([N+]([O-])=O)[CH:9]=[CH:8][N+:7]=1[O-:15].C[O-].[Na+].CO.C[C:22](O)=[O:23]>>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([O:23][CH3:22])[CH:9]=[CH:8][N+:7]=1[O-:15]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 178526749HCID 178526749, compound

Product 1

HCID 178493295HCID 178493295, compoundYield 116%

Procedure

A solution of 2-[(3-hydroxy-1-propyl)amino]-4-nitropyridine-N-oxide (0.275 g, 1 mmol) and 0.5 M NaOMe in MeOH (16 mL, 8 mmol) was heated at reflux under argon for 3 hr. The reaction was then allowed to cool, and glacial AcOH (0.5 mL, 8 mmol) was added. The solution was concentrated to dryness and the residue was triturated with CH2Cl2. The insoluble materials were removed by filtration and the filtrate was concentrated. Silica gel chromatography (5-15% MeOH/CH2Cl2) gave the title compound (0.23 g, 90%) as a colorless oil: MS (ES) m/e 199.0 (M+H)+.

Workup

  1. temperatureat reflux under argon for 3 hr
  2. temperatureto cool
  3. concentrationThe solution was concentrated to dryness
  4. customthe residue was triturated with CH2Cl2
  5. customThe insoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef8d5997d3c14ca196d1caa4600b51d8
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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