4-Nitrobenzaldehyde → HCID 178492967, compound

HRID 2218429Notes

Reaction equation

HRID 2218429 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([O-:14])=[O:13]>CN(C=O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]2[N:9]=[C:19]([C:18]3[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 57482673HCID 57482673, compound

Product 1

HCID 178492967HCID 178492967, compound

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

5-Chloro-4-methoxypyridin-2,3-diamine (0.500 g, 2.88 mmol) was dissolved in DMF (7 ml). Iron(III)chloride hexahydrate (0.062 g, 0.23 mmol) was added and the mixture heated to 80° C. 4-Nitrobenzaldehyde (0.434 g, 2.87 mmol) dissolved in DMF (4 ml) was added dropwise, and the reaction mixture was heated at 110° C. for 11 h with air bubbling through the solution. The DMF was removed by evaporation, the solid residue was dissolved in warm methanol and filtered through a short plug of silica gel. Following evaporation and recrystallization (methanol) the subtitle compound was isolated. Yield: 0.569 g (65%).

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction mixture was heated at 110° C. for 11 h with air
  3. custombubbling through the solution
  4. customThe DMF was removed by evaporation
  5. dissolutionthe solid residue was dissolved in warm methanol
  6. filtrationfiltered through a short plug of silica gel
  7. customevaporation and recrystallization (methanol) the subtitle compound
  8. customwas isolated

Sources & evidence

ORD record
ord-f8f983c3ce894c04ace986b844795605
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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