Ammonium Chloride → 2-Methoxy-3,5-dinitropyridine

HRID 1768505Notes

Reaction equation

HRID 1768505 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][N:6]=1.[Cl-].[NH4+]>CO>[CH3:1][O:2][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 757382-Chloro-3,5-dinitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 5979602-Methoxy-3,5-dinitropyridineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 14% methanol solution of sodium methoxide was added to 25.0 g (120 mmol) of 2-chloro-3,5-dinitropyridine, and the mixture was stirred for 15 minutes at room temperature. The mixture was added to 200 ml of a saturated aqueous ammonium chloride solution, and extracted with 200 ml of ethyl acetate. Washing with saturated saline, drying over anhydrous sodium sulfate, filtering and distilling under reduced pressure (bath temp. 40°-60° C., 40-20 mmHg) yielded yellow crystals, which were recrystallized from methanol to obtain 19.5 g (91.8 mmol) of 2-methoxy-3,5-dinitropyridine as pale yellow crystals (yield: 80%).

Workup

  1. extractionextracted with 200 ml of ethyl acetate
  2. washWashing with saturated saline
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationfiltering
  5. distillationdistilling under reduced pressure (bath temp. 40°-60° C., 40-20 mmHg)
  6. customyielded yellow crystals, which
  7. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-58d721fc3de44c3c95734b27062e57e2
Source dataset
uspto-grants-1995_01
Patent number
US05378244

Reaction notes

Loading…