Hydrochloride methanol → HCID 67800902, compound

HRID 1900854Notes

Reaction equation

HRID 1900854 reaction equation
[N:1]([CH2:4][C:5]1([CH3:24])[O:22][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH:6]1[CH3:23])[NH:13][C:12](=[O:18])[C:11]([CH:19]([CH3:21])[CH3:20])=[CH:10]3)=[N+]=[N-].[H][H].[ClH:27].CO>CN(C)C=O.CO.[Pd]>[NH2:1][CH2:4][C:5]1([CH3:24])[O:22][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH:6]1[CH3:23])[NH:13][C:12](=[O:18])[C:11]([CH:19]([CH3:20])[CH3:21])=[CH:10]3.[ClH:27]

Participants

7

Reactant 3

HCID 21893726Hydrochloride methanolHCID 23369805HCID 23369805, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67800902HCID 67800902, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2-Azidomethyl-8-isopropyl-2,3,5-trimethyl-6,7-dihydrofuro[2,3-f]quinoline-7-one (1.25 g, 3.83 mmol) was dissolved in dimethylformamide (200 ml). To the solution, 10% palladium-on-carbon (1.45 g) was added, followed by stirring at room temperature for 90 minutes in the atmosphere of hydrogen. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The resultant residue was suspended in methanol (50 ml), and the suspension was dissolved with 1.37 N HCl-methanol (4 ml, 5.31 mmol). The reaction mixture was condensed under reduced pressure, and the residue was recrystallized from methanol-ether to obtain 1.08 g of the title compound as colorless powdery crystals (83.7%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. customcondensed under reduced pressure
  4. customthe residue was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-b3516a69f7574ae29196ccee6a1eacb7
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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