Ethanol → Ethyl 5-nitropicolinate

HRID 2409635Notes

Reaction equation

HRID 2409635 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].OS(O)(=O)=O.[CH3:18][CH2:19]O>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:18]([O:11][C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)=[O:12])[CH3:19]

Participants

6

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5204885-Nitropicolinic acid

Product 1

HCID 45116302Ethyl 5-nitropicolinate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-nitro-pyridine-2-carboxylic acid (Step 39.5) (5.74 g, 34.2 mmol), H2SO4 (1 mL) and EtOH (50 mL) was stirred for 1.5 h at reflux. The residue was diluted with EtOAc and saturated solution of NaHCO3. The aqueous layer was separated and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to afford 6.1 g of the title compound as a white solid: ES-MS: 197.1 [M+H]+; tR=3.22 min (System 1).

Workup

  1. temperatureat reflux
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d752ba6b47244b178b1763ced3ba654b
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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