Nitric Acid → HCID 118046196, compound

HRID 1772892Notes

Reaction equation

HRID 1772892 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][CH:6]=[CH:5][N:4]=1.[N+:13]([O-])([OH:15])=[O:14]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][C:6]([N+:13]([O-:15])=[O:14])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 59218646N-(2-Methoxypyridin-3-yl)acetamide

Product 1

HCID 118046196HCID 118046196, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent2×

Procedure

To a stirred solution of N-(2-methoxypyridin-3-yl)acetamide (23 g, 139 mmol) in trifluoroacetic anhydride (TFAA) (90 mL) was added a solution of HNO3 (5.84 mL, 139 mmol) in TFAA (140 mL) dropwise at rt. The reaction was stirred for 1.5 h at rt before being poured into an ice bath with stirring. The precipitated solid was filtered and washed with Et2O (50 mL), then dissolved in EtOAc (1 L) and washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL). The phases were separated and the organic phase dried (MgSO4), and concentrated in vacuo to yield the title compound as a light yellow solid (21.2 g, 100.4 mmol).

Workup

  1. additionbefore being poured into an ice bath
  2. stirringwith stirring
  3. filtrationThe precipitated solid was filtered
  4. washwashed with Et2O (50 mL)
  5. dissolutiondissolved in EtOAc (1 L)
  6. washwashed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL)
  7. customThe phases were separated
  8. dry with materialthe organic phase dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6b2550a4532481dbac0a5c968711399
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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