Hydrochloric Acid → 2-Aminomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one.HCl

HRID 1900812Notes

Reaction equation

HRID 1900812 reaction equation
[N:1]([CH2:4][CH:5]1[O:20][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])[C:11]([CH3:19])=[CH:10]3)=[N+]=[N-].[H][H].[ClH:23]>O1CCCC1.[Pd]>[NH2:1][CH2:4][CH:5]1[O:20][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])[C:11]([CH3:19])=[CH:10]3.[ClH:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 233697942-Azidomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 678029552-Aminomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one.HClYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Azidomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (2.76 g, 10.2 mmol) was dissolved in tetrahydrofuran (200 ml), to which 10% palladium-on-carbon (2.76 g) was added. The mixture was stirred at room temperature for 2 hours in the atmospher of hydrogen. The catalyst was filtered off, and the filtrate was condensed. The residue was converted to a hydrochloric acid salt, and then subjected to recrystallization (methanol-ether) to obtain 2.10 g of the title compound as yellow crystals (73.4%).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customcondensed
  4. customsubjected to recrystallization (methanol-ether)

Sources & evidence

ORD record
ord-7c3250196be54bc4a9025e41bb5d35e5
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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