Hydrochloric Acid → HCID 178470135, compound

HRID 37512Notes

Reaction equation

HRID 37512 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([SH:26])=[N:8][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-])=O)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].Cl>C(O)C>[NH2:17][C:10]1[C:9]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:8][C:7]([SH:26])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470136HCID 178470136, compound

Product 1

HCID 178470135HCID 178470135, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.30 g of 3,4-diethoxycarbonyl-2-mercapto-5-nitro-6-phenylpyridine, 0.41 g of reduced iron and 7 ml of ethanol was heated to 60° C., followed by addition of 1.7 ml of conc. hydrochloric acid. The mixture was heated under reflux for 30 minutes. After the reaction mixture was concentrated, the concentrate was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over magnesium sulfate. The concentrate was subjected to silica gel column chromatography with chloroform as the eluent, to give 0.21 g of the title compound as a yellowish orange viscous oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-ff5f3b2a66f14aef9fcff6889f3ff933
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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