Sodium Hydroxide → Sodium 5-nitropyridine-2,3-dicarboxylate

HRID 619698Notes

Reaction equation

HRID 619698 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:15]([O:17]CC)=[O:16])[C:7]([C:10]([O:12]CC)=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+:21]>O>[N+:1]([C:4]1[CH:5]=[C:6]([C:15]([O-:17])=[O:16])[C:7]([C:10]([O-:12])=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].[Na+:21].[Na+:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15451770Diethyl 5-nitropyridine-2,3-dicarboxylate

Product 1

HCID 70346302Sodium 5-nitropyridine-2,3-dicarboxylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 g (0.168 mol) of diethyl 5-nitropyridine-2,3-dicarboxylate were added in the course of 10 minutes with stirring to a mixture of 13.4 g (0.336 mol) of sodium hydroxide in 65 ml of water and washed in with 6.5 ml of ethanol. The mixture was brought to reflux, diluted with a further 30 ml of water and cooled again after heating for 1 hour. The precipitate deposited after the addition of 500 ml of acetone was filtered off with suction, washed and dried, 42.4 g (98.6% of theory) of sodium 5-nitropyridine-2,3-dicarboxylate of m.p. >260° C. being obtained.

Workup

  1. washwashed in with 6.5 ml of ethanol
  2. temperatureto reflux
  3. additiondiluted with a further 30 ml of water
  4. temperaturecooled again
  5. temperatureafter heating for 1 hour
  6. additionafter the addition of 500 ml of acetone
  7. filtrationwas filtered off with suction
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-56f9108814344af880792f2047661eda
Source dataset
uspto-grants-1999_09
Patent number
US05959116

Reaction notes

Loading…