Ethanol → Ethyl 5-nitropicolinate

HRID 2391788Notes

Reaction equation

HRID 2391788 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-46261e88b00c4b23aa6d89c3ee8a4d9b
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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