Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate → Methyl 7-amino-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927915Notes

Reaction equation

HRID 927915 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([C:6]3[CH:18]=[CH:17][O:16][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H][H]>O1CCOCC1.C(O)(=O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([C:6]3[CH2:18][CH2:17][O:16][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 66685912Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86713283Methyl 7-amino-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylateYield 58.5%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate (Intermediate 24, 1.13 g) in a mixture of dioxane (5 mL) and acetic acid (5 mL) was treated under an atmosphere of nitrogen with palladium hydroxide on carbon (10%, 0.1 g). The nitrogen was replaced by hydrogen and the mixture was stirred under an atmosphere of hydrogen for 24 hours. The mixture was diluted with ethyl acetate and filtered through Celite and the filtrate was washed with 1M aqueous sodium hydroxide solution, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%. The isolated product was triturated with a mixture of ether and cyclohexane and the solid was collected by filtration to give methyl 7-amino-1,2-dihydrofuro[2,3-c]quinoline-6-carboxylate (0.666 g) as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. washthe filtrate was washed with 1M aqueous sodium hydroxide solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%
  7. customThe isolated product was triturated with a mixture of ether and cyclohexane
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-f22f142c71474824a60a84b13ff05acb
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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