Sodium Hydroxide → 2-Methyl-5-nitropyridine

HRID 1080197Notes

Reaction equation

HRID 1080197 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10](CC([O-])=O)CC([O-])=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 196914242-(5-Nitro-2-pyridyl)-1,3-propanedicarboxylate

Product 1

HCID 27945522-Methyl-5-nitropyridineYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 102.0 g (0.361 mol) of 2-(5-nitro-2-pyridyl)-1,3-propanedicarboxylate, from Step 1, in 600 mL of 20% aqueous sulfuric acid solution was heated at 95° C. for 24 hours. The resultant solution was poured onto 1 kg of ice and the aqueous mixture was adjusted to a pH within the range pH 10-12 with 50% aqueous sodium hydroxide solution. The precipitate was filtered and dissolved in ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated to a solid residue. The residue was washed with hexane. The hexane was removed by filtration and the solid was dried to afford 45.86 g (92% yield) of the title compound; 1H NMR (CDCl3) d 2.71 (s, 3H), 7.36 (d, 1H, J=9.0 Hz), 8.37 (dd, 1H, J=3.0 Hz, 9.0 Hz), 9.33 (d, 1H, J=3.0 Hz).

Workup

  1. filtrationThe precipitate was filtered
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid residue
  6. washThe residue was washed with hexane
  7. customThe hexane was removed by filtration
  8. customthe solid was dried

Sources & evidence

ORD record
ord-86f646d1af5d488f983a0dcdbba94b0b
Source dataset
uspto-grants-1996_12
Patent number
US05580872

Reaction notes

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