Sulfuric Acid → Methyl 5-nitropicolinate

HRID 1892578Notes

Reaction equation

HRID 1892578 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].S(=O)(=O)(O)O.[C:18](=O)([O-])[O-].[Na+].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:18])=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 5204885-Nitropicolinic acid

Product 1

HCID 12457882Methyl 5-nitropicolinateYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Nitropyridine-2-carboxylic acid (100 g, 0.60 mol) was heated at reflux in methanol (1 L) and sulfuric acid (57 mL) for 5 hours. The reaction mixture was cooled, reduced to half volume in vacuo, and the residue neutralized with a solution of sodium carbonate. The resulting precipitate was filtered to give methyl 5-nitropyridine-2-carboxylate (yield 89%, 98 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-5cb26fab50964084badf65cf6be9eb45
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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