Water → 6-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-3-amine

HRID 1433396Notes

Reaction equation

HRID 1433396 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=1.[Cl-].[NH4+].O>C(O)C.C(OCC)(=O)C.CCCCCC.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[N:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=1

Participants

8

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 229362516,7-Dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinoline

Product 1

HCID 229365976-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-3-amineYield 64%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dimethoxy-4-((5-nitro-2-pyridyl)oxy)quinoline (654 mg, 2.00 mmol), iron powder (559 mg, 10.0 mmol) and ammonium chloride (1.07 g, 20.0 mmol) were heated and stirred in ethanol (20 ml)-water (5 ml) at 80° C. for 20 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. After washing the organic layer with water and saturated brine 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 suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out and washed with ethyl acetate and then blow-dried to obtain the title compound (380 mg, 1.28 mmol, 64%) as light yellow crystals.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered with celite
  3. washwashed in ethyl acetate
  4. washAfter washing the organic layer with water and saturated brine
  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. filtrationthe crystals were filtered out
  10. washwashed with ethyl acetate
  11. customblow-dried

Sources & evidence

ORD record
ord-11024cadad5b4676b4092537191646ba
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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