Nitric Acid → HCID 178433475, compound

HRID 541419Notes

Reaction equation

HRID 541419 reaction equation
[OH:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[OH:1][C:2]1[N:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178425908HCID 178425908, compound

Product 1

HCID 178433475HCID 178433475, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 2-hydroxy-6-methylnicotinic acid (14.0 g, 91.5 mmol, 1.00 equiv) in sulfuric acid (conc.) (140 mL) at 0° C. was added dropwise a solution of HNO3 (12.0 g, 190 mmol, 2.00 equiv) in sulfuric acid (conc.) (10 mL). The resulting mixture was then stirred for 2 h at 90° C., cooled to ambient temperature, and then quenched with 250 mL of ice water. The resulting solids were collected by filtration and dried in an oven under reduced pressure to yield 15.8 g (87%) of the title compound as a yellow solid.

Workup

  1. temperaturecooled to ambient temperature
  2. customquenched with 250 mL of ice water
  3. filtrationThe resulting solids were collected by filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-e5cf01cd3b4b4d03b11cb49e81b5cb2e
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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