Nitric Acid → 4,6-Dihydroxy-5-nitro-2-trifluoromethyl-nicotinic acid ethyl ester

HRID 639705Notes

Reaction equation

HRID 639705 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[C:10]([OH:11])=[CH:9][C:8]([OH:12])=[N:7][C:6]=1[C:13]([F:16])([F:15])[F:14])[CH3:2].[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[C:10]([OH:11])=[C:9]([N+:18]([O-:20])=[O:19])[C:8]([OH:12])=[N:7][C:6]=1[C:13]([F:14])([F:15])[F:16])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178470040HCID 178470040, compound

Product 1

HCID 1784691454,6-Dihydroxy-5-nitro-2-trifluoromethyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4,6-dihydroxy-2-trifluoromethyl-nicotinic acid ethyl ester (1 g, 3.9 mmol) was dissolved in 10 mL of concentrated sulfuric acid and 2 mL of fuming nitric acid was added dropwise at room temperature. Once the addition was complete, the mixture was stirred at room temperature for 30 minutes. The mixture was then poured into crushed ice and the white precipitate was collected, dissolved in 50 mL of ethyl acetate, washed with 50 mL of water and 50 mL of brine, dried over magnesium sulfate and the solvent was removed in vacuo to give 1.1 g of the title compound as a white solid.

Workup

  1. additionOnce the addition
  2. additionThe mixture was then poured
  3. custominto crushed ice
  4. customthe white precipitate was collected
  5. dissolutiondissolved in 50 mL of ethyl acetate
  6. washwashed with 50 mL of water and 50 mL of brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-60eb538ffc4545fc80187be09bb4af56
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

Loading…