2-Azidomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one → 2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

HRID 1900716

Reaction equation

HRID 1900716 reaction equation
[N:1]([CH2:4][CH:5]1[O:19][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)=[N+]=[N-].[H][H]>CN(C)C=O.[Pd]>[NH2:1][CH2:4][CH:5]1[O:19][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3

Participants

5

Reactant 2

HCID 233697182-Azidomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 233695672-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Azidomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (759 mg) was dissolved in dimethylformamide (20 ml). To the solution, 10% palladium-on-carbon (455 mg) was added, and the solution was hydrogenated in the atmosphere of hydrogen at ambient temperature and under atmospheric pressure. After completion of the reaction, the catalyst was filtered off. When the solvent was evaporated, 0.7 g of the title compound was obtained as a crude product. This product was purified by silica gel column chromatography to obtain 409 mg of a free base (60.0%). The obtained free base was converted into a hydrochloric acid salt, followed by recrystallizing from a solvent mixture of methanol-diethylether, obtaining yellow powdery crystals having a melting point over 300° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. customWhen the solvent was evaporated

Sources & evidence

ORD record
ord-071ca108d66c46a7856cd12d5b1c6ef7
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Linked notes

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