Hydrochloric Acid → HCID 15289694, compound

HRID 37484Notes

Reaction equation

HRID 37484 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:3]=1.Cl>C(O)C>[NH2:18][C:5]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[N:3][C:2]([Cl:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19935610HCID 19935610, compound

Product 1

HCID 15289694HCID 15289694, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

In 4 ml of ethanol was dissolved 280 mg of 2-chloro-3,4-diethyoxycarbonyl-6-(4-methoxyphenyl)-5nitropyridine, whereto 340 mg(8.9 eq.) of reduced iron was added. After the mixture was heated to 60° C., 1.5 ml of conc. hydrochloric acid was added dropwise and the mixture was refluxed. After heating for 20 minutes, the solvent was distilled off. The residue was neutralized with an aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. After the precipitate was filtered off, the obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. Thereafter, the solvent was distilled off.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed
  3. temperatureAfter heating for 20 minutes
  4. distillationthe solvent was distilled off
  5. extractionfollowed by extraction with ethyl acetate
  6. filtrationAfter the precipitate was filtered off
  7. washthe obtained organic layer was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride, and dried
  9. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-34f59da3e57f4135b40663cb60f9376a
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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