Sodium Nitrate → HCID 178469717, compound

HRID 1974812Notes

Reaction equation

HRID 1974812 reaction equation
[CH2:1]([C:3]1[S:17][C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([OH:11])=[C:5]2[CH:4]=1)[CH3:2].[N+:18]([O-])([O-:20])=[O:19].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[S:17][C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([OH:11])=[C:5]2[C:4]=1[N+:18]([O-:20])=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 178469716HCID 178469716, compound

Product 1

HCID 178469717HCID 178469717, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of ethyl 2-ethyl-4-hydroxythieno[2,3-b]pyridine-5-carboxylate (1.0 g, 4.0 mmol) in conc. sulfuric acid (10 ml) was cooled to -5° C. and a solution of sodium nitrate (370 mg, 4.3 mmol) in conc. sulfuric acid (5 ml) was added dropwise to the chilled solution. The reaction mixture was stirred at -3° C. to -5° C. for 1 hour and poured into ice-water. The precipitated product was collected by filtration and washed with cold water and then ethanol. The resulting precipitate was dissolved in chloroform, washed with a saturated aqueous sodium chloride, dried (MgSO4) and evaporated in vacuo. The resulting yellow solid was washed with a mixture of ether/hexane, and dried to give 960 mg (81%) of the title compound.

Workup

  1. filtrationThe precipitated product was collected by filtration
  2. washwashed with cold water
  3. dissolutionThe resulting precipitate was dissolved in chloroform
  4. washwashed with a saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. washThe resulting yellow solid was washed with a mixture of ether/hexane
  8. customdried

Sources & evidence

ORD record
ord-6f42ea7a70544612aab451df925ad4d9
Source dataset
uspto-grants-1994_02
Patent number
US05284661

Reaction notes

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