Nitric Acid → HCID 22615159, compound

HRID 469819Notes

Reaction equation

HRID 469819 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[N+:14]([O-:17])([OH:16])=[O:15]>>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:4][N:3]=1.[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([N+:14]([O-:17])=[O:15])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 230702-Bromo-3-pyridinol

Product 2

HCID 22615159HCID 22615159, compoundHCID 53416660HCID 53416660, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 13 g (73.2 mmol) 2-bromo-3-pyridinol (Fluka 18292) in 40 ml of cone, sulfuric acid 5.1 ml (74 mmol) of nitric acid (65%) are added at 0° C. The reaction mixture is stirred at 0° C. for 12 h, then poured on water and extracted 2× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, EtOAc) to afford 5.3 g of 2-bromo-4-nitro-pyridin-3-ol and 2 g of 2-bromo-6-nitro-pyridin-3-ol.

Workup

  1. additionpoured on water
  2. extractionextracted 2× with EtOAc
  3. washThe combined organic layers are washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by chromatography (silicagel, EtOAc)

Sources & evidence

ORD record
ord-91d4974dc56348cda52148486eebe238
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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