Methyl 6-chloro-5-nitronicotinate → HCID 178498866, compound

HRID 1059297Notes

Reaction equation

HRID 1059297 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[SH2:15].[Na]>CO>[NH2:12][C:11]1[C:2]([SH:15])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178498866HCID 178498866, compoundYield 484%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6 g of methyl 6-chloro-5-nitronicotinate in methanol (100 ml) was added 6.7 g of sodium hydrogensulfide and the resulting mixture was heated under reflux for 2 hours. After distilling off the solvent under reduced pressure, dilute hydrochloric acid was added to the residue followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 24.7 g of the title compound as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationAfter distilling off the solvent under reduced pressure, dilute hydrochloric acid
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionDiisopropyl ether was added to the residue
  9. customthe crystals thus precipitated
  10. filtrationwere taken up by filtration

Sources & evidence

ORD record
ord-02e42ce3942a4261a0d0b1bb1124a0c9
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…