Nitric Acid → HCID 178524776, compound

HRID 1419177Notes

Reaction equation

HRID 1419177 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[N+:11]([O-])([OH:13])=[O:12]>>[OH:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178524776HCID 178524776, compoundYield 23%

Conditions

Temperature
50 °C

Procedure

A mixture of 6-hydroxynicotinic acid (16.60 g, 0.119 mol) and fuming nitric acid (166 mL) was heated at 50° C. for 4 hours. The resulting reaction solution was cooled to room temperature, and then carefully added to ice (300 g). The resultant mixture was then stored at 10° C. overnight, and the precipitated solid was filtered and dried in vacu to afford the title compound (5.50 g, 0.027 mol, 23%) as a yellow solid: 1H NMR (DMSO-d6) δ 13.4 (br s, 2H), 8.64 (d, J=2.2 Hz, 1H), 8.37 (d, J=2.2 Hz, 1H); 13C NMR (DMSO-d6) δ 164.1, 154.4, 146.1, 138.5, 137.2, 107.9. HRMS calculated for C6H4N2O5 184.0120, found 184.0134. Anal. calcd for C6H4N2O5 : C, 39.14; H, 2.19; N, 15.21. Found: C, 39.21; H, 2.33; N, 15.56.

Workup

  1. customThe resulting reaction solution
  2. temperaturewas cooled to room temperature
  3. filtrationthe precipitated solid was filtered
  4. customdried in vacu

Sources & evidence

ORD record
ord-b7f734911ca8439e8033b82eae46ac85
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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