Hydrochloric Acid → HCID 70186511, compound

HRID 1069443Notes

Reaction equation

HRID 1069443 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:13])[C:5]([N+:14]([O-])=O)=[C:4]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1.Cl>CO.O.[Zn]>[NH2:14][C:5]1[C:6](=[O:13])[N:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:2]([CH3:1])=[CH:3][C:4]=1[S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86757069HCID 86757069, compound

Product 1

HCID 70186511HCID 70186511, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

4.67 g (14 mmol) of methyl 6-methyl-3-nitro-2-oxo-4-(phenylthio)-1,2-dihydropyridine-1-acetate are suspended in 200 ml of a methanol:water (1:1) mixture, 5 ml of a 2 N aqueous hydrochloric acid solution and 5 g (76.4 mmol) of zinc are added successively and the mixture is heated at the reflux temperature for 3 hours. The reaction medium is allowed to cool, filtered and the solvent is evaporated. The medium is neutralized with 200 ml of sodium hydrogen carbonate and extracted with twice 100 ml of dichloromethane. The organic phase is recovered and it is dried and evaporated. The residue is purified by chromatography on a silica gel column, eluting with a dichloromethane:methanol (98:2) mixture. 2 g of product are obtained in the form of a white solid which are recrystallized from ethanol.

Workup

  1. additionare added successively
  2. temperaturethe mixture is heated at the reflux temperature for 3 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. extractionextracted with twice 100 ml of dichloromethane
  7. customThe organic phase is recovered
  8. customit is dried
  9. customevaporated
  10. customThe residue is purified by chromatography on a silica gel column
  11. washeluting with a dichloromethane:methanol (98:2) mixture

Sources & evidence

ORD record
ord-5054307022dd4bca804cf282c4a622c3
Source dataset
uspto-grants-2001_06
Patent number
US06252082B1

Reaction notes

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