4-(2-Methoxy-4-methylmercapto-benzoylamino)-5-nitro-1H-pyridin-2-one → 2-(2-Methoxy-4-methylmercapto-phenyl)-5H-imidazo[4,5-c]-pyridin-6-one

HRID 1589296Notes

Reaction equation

HRID 1589296 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:4]=1[C:5]([NH:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][NH:11][C:10](=[O:17])[CH:9]=1)=O>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:4]=1[C:5]1[N:14]=[C:13]2[CH2:12][NH:11][C:10](=[O:17])[CH:9]=[C:8]2[N:7]=1

Participants

4

Reactant 1

HCID 135209344-(2-Methoxy-4-methylmercapto-benzoylamino)-5-nitro-1H-pyridin-2-one

Product 1

HCID 704558092-(2-Methoxy-4-methylmercapto-phenyl)-5H-imidazo[4,5-c]-pyridin-6-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

0.6 g of crude 4-(2-methoxy-4-methylmercapto-benzoylamino)-5-nitro-1H-pyridin-2-one were dissolved in 10 ml of glacial acetic acid, the solution was mixed with two spatula tipsful of iron powder, and the mixture was stirred for 30 minutes at room temperature. The mixture was then refluxed for 20 minutes, filtered, and the filtrate was evaporated in vacuo. The product thus obtained were purified by chromatography on silica gel (eluant: methylene chloride/ethanol=100:2 to 100:15).

Workup

  1. temperatureThe mixture was then refluxed for 20 minutes
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. customThe product thus obtained
  5. customwere purified by chromatography on silica gel (eluant: methylene chloride/ethanol=100:2 to 100:15)

Sources & evidence

ORD record
ord-18630330845a4e4cb0b76e3da355b2ef
Source dataset
uspto-grants-1986_02
Patent number
US04568680

Reaction notes

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