Ammonium nitrate → 3-Pyridinecarboxylic acid, 2-ethoxy-5-nitro-, ethyl ester

HRID 2407769Notes

Reaction equation

HRID 2407769 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[NH4+].[CH2:6]([O:8][C:9]1[N:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:7]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH2:6]([O:8][C:9]1[N:19]=[CH:18][C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:7]

Participants

4

Reactant 2

HCID 22985Ammonium nitrateHCID 12326832Ethyl 2-ethoxypyridine-3-carboxylate

Product 1

HCID 104442903-Pyridinecarboxylic acid, 2-ethoxy-5-nitro-, ethyl esterYield 56.3%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

Ammonium nitrate (1.11 g) was added portionwise to an ice-cooled solution of the compound prepared in Example 285 (0.900 g) in trifluoroacetic anhydride (11.5 mL). The mixture was stirred at room temperature overnight and then carefully poured into ice-water and the resulting suspension stirred for an hour. The precipitate was collected by filtration and washed with water. The solids were dried under vacuo to obtain the title compound (0.624 g) having the following physical data.

Workup

  1. stirringthe resulting suspension stirred for an hour
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customThe solids were dried under vacuo

Sources & evidence

ORD record
ord-530e13399932498fa2da854c78a783b1
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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