Water → HCID 22936458, compound

HRID 387747Notes

Reaction equation

HRID 387747 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:23]([NH2:25])=[O:24].[Cl-].[NH4+].O.C(OCC)(=O)C>C(O)C.[Fe].CO>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:23]([NH2:25])=[O:24])[CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[N:15][CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 22936345HCID 22936345, compound

Product 1

HCID 22936458HCID 22936458, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

7-Methoxy-4-((5-nitro-2-pyridyl)oxy)-6-quinolinecarboxamide (93.0 mg, 273 mmol), iron powder (76.0 mg, 1.36 mmol) and ammonium chloride (146 mg, 2.73 mmol) were heated and stirred in ethanol (4 ml)-water (1 ml) at 80° C. for 20 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in an ethyl acetate-tetrahydrofuran mixed solvent. After washing the organic layer with water and saturated saline and drying over anhydrous magnesium sulfate, the drying agent was filtered out and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:methanol=20:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (61.0 mg, 197 mmol, 72%) as yellow crystals.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered with celite
  3. washwashed in an ethyl acetate-tetrahydrofuran mixed solvent
  4. washAfter washing the organic layer with water and saturated saline
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. filtrationthe drying agent was filtered out
  7. distillationthe filtrate was distilled off under reduced pressure
  8. customThe obtained crude product
  9. additionthe fraction containing the target substance
  10. concentrationwas concentrated
  11. additiondiluted with hexane
  12. filtrationafter which the crystals were filtered out
  13. washwashed with hexane
  14. customblow-dried

Sources & evidence

ORD record
ord-358b056709f54ebdbad4430539ac8b65
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

Loading…